Cerium (iv) complexes and their use in organic electronics

ABSTRACT

The present invention relates to an electronic component comprising a cerium IV complex, a doped semi-conductor matrix material comprising the cerium IV complex and at least one electron donor, the use of the cerium IV complex, especially as an organic semi-conductor, as a dopant in organic semiconductor matrix materials and as a charge injector in a charge injection layer, and new cerium IV complexes.

The present invention relates to electronically doped semiconductormaterials and an electronic component comprising cerium (IV) complexes.A further object of the invention is the use of the cerium (IV)complexes as electron acceptors, especially as p-dopants and electrontransport materials in organic electronic components. Another object ofthe invention are new cerium (IV) complexes.

BACKGROUND OF THE INVENTION

Organic electronics focuses on the development, characterization andapplication of new materials, both based on small organic molecules andpolymers with certain desired electronic properties for the productionof electronic components. These comprise e.g. organic field effecttransistors (OFETs) such as organic thin film transistors (OTFTs),organic electroluminescent devices such as organic light emitting diodes(OLEDs), organic solar cells (OSCs), e.g. exciton solar cells,dye-sensitized solar cells (DSSCs) or perovskite solar cells,electrophotography, e.g. photoconductive materials in organicphotoconductors (OPCs), organic optical detectors, organicphotoreceptors, light-emitting electrochemical cells (LECs) and organiclaser diodes.

It is known that organic semiconductor matrices can be heavilyinfluenced regarding their electrical conductivity by doping. Suchorganic semiconductive matrix materials can be formed by either fromcompounds with good electron donor properties (p-conductor) or fromcompounds with good electron acceptor properties (n-conductor). Incontrast to inorganic semiconductors, organic semiconductors have a verylow intrinsic charge carrier concentration. Organic semi-conductormatrix materials are therefore usually doped in order to achieve goodsemiconductor properties. For n-doping strong electron donors (ndopants) are used, which transfer an electron to the LUMO of thesemiconductor matrix (n-doping), resulting in a free electron on thematrix (SOMO). For p-doping strong electron acceptors (p-dopants) areused, which remove an electron from the HOMO of the semiconductor matrix(p-doping), resulting in a hole. In other words, for p-doping the LUMOof the dopant must be below the HOMO-energy of the matrix. The dopantacts as an acceptor and leaves a mobile hole (SOMO) in the matrix.

Known p-dopants for electron donor materials are electron acceptors suchas tetracyanoquinone methane (TCNQ),2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone methane (F4TCNQ),trinaphthylenes (HATNA), metal oxides such as MoO₃ or WO₃, or radialenecompounds as e.g. described in EP 2180029. The acceptor moleculesgenerate so-called holes in the semiconductor matrix materials (holetransport materials) by electron transfer processes, and theconductivity of the semiconductor matrix material (hole transportmaterial) is more or less changed depending on the number and mobilityof the holes.

However, the previously described compounds or compound classes havedisadvantages for a technical use in the production of dopedsemiconductors or of corresponding electronic components with such dopedlayers. The compounds or compound classes mentioned are, for example,too volatile, have a too high absorption coefficient, have an unstableevaporation rate and/or show low thermostability. In addition, some ofthese compounds have very high production costs.

Thus, there is still a demand for compounds, which are easily availableor producible, are suitable for doping electron donor materials and donot have the disadvantages described above.

Only a few cerium (IV) complexes of the class of diketonates are known.A few β-diketonate complexes of cerium (IV) are described in theliterature. M. Ciampolini et al., J. C. S. Dalton, 1977, 1325; T. J.Pinnaviaia et al., Contribution from the department of Chemistry,Cornell University, Ithaca, N.Y., 1965, 233; I. Baxter et al., J. Chem.Cryst, Vol. 28, No 4, 1998, 267; N. A. Piro et al., Coord. Chem. Review,260, 2014, 21, M. Delarosa et al., J. Coord. Chem., 55(7), 2002, 781;Jahr et al., Zeitschrift für Chemie, Bd. 15, 1975, S 280-281; Snezhko etal. Material Science and Engineering, Vol. 18, 1993, S. 230-231; Brillet al., Liebigs Annalen der Chemie, 1979, S. 803-810 and WO02/018394describe the following cerium (IV) complexes:

WO02/018394 relates to precursor source reagent metal-organiccompositions. The formation of cerium doped (Ca, Sr)Ga₂S₂ films withthio-containing solvent systems and deposition in the presence ofhydrogen sulfide gas is described.

Kunkely et al., Journal of Photochemistry and Photobiology A, Vol 146,No 1-2, p. 63-66 describes cerium (IV)2,2,6,6-tetramethyl-3,5-heptane-dionate anion. It is further describedthat this complex has luminescent properties and is also photoactive.These properties are irrelevant for a p-dopant or for redox doping pairsof transport layers.

US 2010/0038632 describes a variety of complexes including cerium (IV)complexes. On the one hand explicit cerium (IV) complexes according tothe invention are not mentioned. On the other hand, the large band gapsin cerium complexes mentioned in this document are not relevant for ap-dopant.

Until now, it was unknown to use cerium (IV) complexes in organicsemiconductor materials. In particular, it has not yet been described touse cerium (IV) complexes as p-dopants, as electron transport materialsor as electron acceptors.

Surprisingly, it has now been found that cerium (IV) complexes can beadvantageously used as p-dopants. Furthermore, it has been found thatcerium (IV) complexes can be used as electron transport materials (ETM)in organic electronic components such as organic light emitting diodes(OLED), photovoltaic cells, organic solar cells (OPV), organic diodes ororganic transistors.

Furthermore, many cerium (IV) diketonates can be evaporated very wellunder vacuum and occasionally exhibit high thermostability. Thus, theyare basically suitable for both variants of processing oforganic-electronic components, the vacuum coating (vapour deposition)and the solvent-based processing (solution processing).

SUMMARY OF THE INVENTION

A first object of the invention is an electronic component comprising acompound of the general formula (I.1)

Ce⁴⁺(L₁L₂L₃L₄)⁴⁻(I.1)

or a mixture of at least two different compounds of the general formula(I.1), wherein L₁; L₂; L₃; and L₄ are independently from each otherselected from a bidentate ligand having the general formula (I.2)

wherein

-   -   X and W independently from each other represent O, S or NR⁶;    -   Y represents N or CR³⁻;    -   R¹, R² independently from each other represent CN, C₁-C₆ alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NW, O, S, SO and SO₂, wherein aryl and hetaryl are unsubstituted        or substituted by 1, 2, 3, 4 or 5 identical or different        radicals R⁸;    -   R³ represents hydrogen, CN, nitro, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NW, O, S, SO and SO₂, wherein aryl and hetaryl are unsubstituted        or substituted by 1, 2, 3, 4 or 5 identical or different        radicals R⁵⁻;    -   R^(4a)R^(4b) independently from each other represent hydrogen,        C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵⁻;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   R⁶ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NW, O, S, SO and SO₂, wherein aryl and hetaryl are unsubstituted        or substituted by 1, 2, 3, 4 or 5 identical or different        radicals R⁵⁻;    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵⁻;    -   R⁸ represents CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or        C₆-C₁₄-aryl, which is unsubstituted or substituted by 1, 2 or 3        identical or different radicals selected from C₁-C₄-alkyl and        C₁-C₄-haloalkyl.

A further object of the invention is an electronic component comprisinga compound of the general formula (I)

or a mixtures thereof, wherein

-   -   X and W independently from each other represent O, S or NR⁶;    -   Y represents N or CR³⁻;    -   R¹, R² independently from each other represent CN, C₁-C₆ alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, N^(4b)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁸;    -   R³ represents hydrogen, CN, nitro, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵;    -   R^(4a)R^(4b) independently from each other represent hydrogen,        C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   R⁶ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻;    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵⁻;    -   R⁸ represents CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or        C₆-C₁₄-aryl, which is unsubstituted or substituted by 1, 2 or 3        identical or different radicals selected from C₁-C₄-alkyl and        C₁-C₄-haloalkyl.

A further object of the invention is an electronic component comprisinga compound of the general formula (I)

or mixtures thereof, wherein

-   -   X and W independently from each other represent 0, S or NR⁶⁻;    -   Y represents N or CR³⁻;    -   R¹, R² independently from each other represent CN,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻;    -   R³ represents hydrogen, CN, nitro, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        O, S, SO and SO₂, wherein aryl and hetaryl are unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵⁻;    -   R^(4a)R^(4b) independently from each other represent hydrogen,        C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵⁻;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   R⁶ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻;    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵.

A further object of the invention is a doped semiconductor matrixmaterial comprising at least one electron donor and at least onecompound of formula (I.1) or (I), wherein the radicals X, W, Y, R¹ andR² have the meanings given above and as defined below.

Another object of the invention is the use of a compound (I.1) ormixtures thereof or compound (I) or mixtures thereof, wherein theradicals X, W, Y, R¹ and R² have the meanings defined before and asdefined below,

-   -   as organic semiconductor,    -   as doping agent in organic semiconductor matrix materials,        especially as p-dopant in hole transport layers,    -   as charge injector in a charge injection layer,    -   as cathode material in organic batteries,    -   as electrochromic material.

A further object of the invention is the use of Ce(III)-complex anionsobtained by reduction of a compound (I.1) or (I) as defined above andbelow or of charge transfer complexes of a compound (I.1) or (I), asdefined above and below, with electron donors as organic conductor, aselectrochromic material or as ferrimagnets.

A further object of the invention is a compound of the general formula(I.1)

Ce⁴⁺(L₁L₂L₃L₄)⁴⁻  (I.1),

and mixtures thereof, wherein

-   -   L₁; L₂; L₃; and L₄ are independently from each other a bidentate        ligand having the general formula (I.2)

wherein

-   -   X and W independently from each other represent 0, S or NR⁶;    -   Y represents N or CR³;    -   R¹, R² independently from each other represent CN,        C₁-C₆-haloalkyl, C₁—O₅-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁸;    -   R³ represents hydrogen, CN, nitro, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆₋C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵;    -   R^(4a)R^(4b) independently from each other represent hydrogen,        C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵⁻;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   R⁶ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        O, S, SO and SO₂, wherein aryl and hetaryl are unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵⁻;    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵⁻;    -   R⁸ represents CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or        C₆-C₁₄-aryl, which is unsubstituted or substituted by 1, 2 or 3        identical or different radicals selected from C₁-C₄-alkyl and        C₁-C₄-haloalkyl;    -   with the proviso that the following compounds are excluded:

A further object of the invention are compounds of the general formula(I)

and their charge transfer complexes, their reduction products andmixtures thereof, wherein

-   -   X and W independently from each other represent 0, S or NR⁶;    -   Y represents N or CR³;    -   R¹, R² independently from each other represent CN, C₁-C₆ alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁸⁻;    -   R³ represents hydrogen, CN, nitro, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻;    -   R^(4a)R^(4b) independently from each other represent hydrogen,        C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵⁻;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   R⁶ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵;    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵⁻;    -   R⁸ represents CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or        C₆-C₁₄-aryl, which is unsubstituted or substituted by 1, 2 or 3        identical or different radicals selected from C₁-C₄-alkyl and        C₁-C₄-haloalkyl;

with the proviso that the following compounds are excluded:

A further object of the invention are compounds of general formula (I)

and their charge transfer complexes, their reduction products andmixtures thereof, wherein

-   -   X and W independently from each other represent 0, S or NR⁶;    -   Y represents N or CR³;    -   R¹, R² independently from each other represent CN, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻;    -   R³ represents hydrogen, CN, nitro, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻;    -   R^(4a)R^(4b) independently from each other represent hydrogen,        C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   R⁶ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵;    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵⁻;

with the proviso that the following compounds are excluded:

DESCRIPTION OF THE INVENTION

The invention has the following advantages:

-   -   The cerium-(IV)-complexes according to the invention have only        low production costs.    -   The cerium-(IV)-complexes according to the invention are        advantageously suitable as electron acceptors for use as        p-dopants and as electron transport materials in        organic-electronic components.    -   The cerium-(IV)-complexes according to the invention exhibit        better conductivity compared to known electron acceptors.    -   The cerium-(IV)-complexes according to the invention show an        improved thermostability of the doped layers compared to the        state of the art.    -   Furthermore, the cerium (IV) complexes according to the        invention are characterized by a higher doping efficiency.    -   The cerium-(IV)-complexes according to the invention show only a        low absorption of the doped layer. Therefore, parasitic        absorption and emissions can be reduced or even prevented.    -   The cerium-(IV)-complexes according to the invention are        suitable for the production of organic and hybrid        opto-electronic components, both by means of solvent processing        and by vacuum reprocessing.

In the context of the invention, a bidentate ligand (also calleddidentate) is a ligand, which binds with two atoms to the metal atom(cerium atom).

In the context of the invention, a homoleptic cerium (IV) compound is acomplex, wherein all ligands are identical.

In the context of the invention, a heteroleptic cerium (IV) compound isa complex, wherein the meaning of at least one ligand is different tothe remaining ligands.

In the context of the invention, the prefix C_(n)-C_(m) indicates thenumber of carbon atoms that a molecule or residue designated thereby maycontain.

In the context of the invention, the expression C₁-C₆-alkyl refers tounbranched or branched saturated hydrocarbon groups having 1 to 6 carbonatoms. C₁-C₆-alkyl are e.g. methyl, ethyl, propyl, 1-methylethyl, butyl,1-methylpropyl, 2-methyl propyl, 1,1-dimethylethyl, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl. C₁-C₄-alkyl refers,e.g. to methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl.

In the context of the invention the expression C₁-C₆-alkoxy refers to anunbranched or branched saturated C₁-C₆-alkyl group as defined above,which is bound via an oxygen atom. Alkoxy radicals with 1 to 4 carbonatoms are preferred, particularly preferred are 1 or 2 carbon atoms.C₁-C₂-alkoxy is methoxy or ethoxy. C₁-C₄-alkoxy is e.g. methoxy, ethoxy,n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy(sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy(tert-butoxy). C₁-C₆-alkoxy comprises the meanings given forC₁-C₄-alkoxy and additionally e.g. pentoxy, 1 methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy and 3,3-dimethylbutoxy.

In the context of the invention the expression C₁-C₆-alkylsulfanylrefers to an unbranched or branched saturated C₁-C₆-alkyl group asdefined above, which is bound via a sulfur atom. Alkylsulfanyl radicalswith 1 to 4 carbon atoms are preferred, particularly preferred are 1 or2 carbon atoms. C₁-C₂-alkylsulfanyl is methylsulfanyl or ethylsulfanyl.C₁-C₄-alkylsulfanyl is e.g. methylsulfanyl, ethylsulfanyl,n-propylsulfanyl, 1-methylethyl-sulfanyl (isopropylsulfanyl),butylsulfanyl, 1-methylpropylsulfonyl (sec-butylsulfanyl),2-methylpropylsulfonyl (isobutylsulfanyl) or 1,1-dimethylethylsulfanyl(tert-butylsulfanyl). C₁-C₆-alkylthio comprises the meanings given forC₁-C₄-alkylsulfanyl and additionally also, e.g., pentylsulfanyl,1-methylbutylsulfanyl, 2-methylbutylsulfanyl, 3-methylbutylsulfanyl,1,1-dimethylpropylsulfanyl, 1,2-dimethylpropylsulfanyl,2,2-dimethylpropylsulfanyl, 1-ethylpropylsulfanyl, hexylsulfanyl,1-methylpentylsulfanyl, 2-methylpentylsulfanyl, 3-methylpentylsulfanyl,4-methylpentylsulfanyl, 1,1-dimethylbutylsulfanyl,1,2-dimethylbutylsulfanyl, 1,3-dimethylbutylsulfanyl,2,2-dimethylbutylsulfanyl, 2,3-dimethylbutylsulfanyl,3,3-dimethylbutylsulfanyl, 1-ethylbutylsulfanyl, 2-ethylbutylsulfanyl,1,1,2-trimethylpropylsulfanyl, 1,2,2-trimethylpropylsulfanyl,1-ethyl-1-methylpropylsulfanyl or 1-ethyl-2-methylpropylsulfanyl.

In the context of the invention the expressions haloalkyl, haloalkoxyand haloalkylsulfanyl refer to partially or fully halogenated alkyl,alkoxy or alkylsulfanyl. In other words, one or more hydrogen atoms, forexample 1, 2, 3, 4 or 5 hydrogen atoms bonded to one or more carbonatoms of alkyl, alkoxy or alkylsulfanyl are replaced by a halogen atom,in particular by fluorine or chlorine.

The expression “halogen” denotes in each case fluorine, chlorine,bromine or iodine.

The expression “CN” denotes the cyano group (—C≡N).

The expression “aryl” comprises in the context of the invention mono- orpolynuclear aromatic hydrocarbon radicals with usually 6 to 14,especially preferably 6 to 10 carbon atoms. Examples of aryl areespecially phenyl, naphthyl, indenyl, fluorenyl, anthracenyl,phenanthrenyl, naphthacenyl, chrysenyl, pyrenyl, etc. and especiallyphenyl or naphthyl.

The expression “hetaryl” comprises in the context of the invention mono-or polynuclear aromatic hydrocarbon radicals with 4 to 13 carbon atoms,wherein 1, 2 or 3 carbon atoms have been replaced by 1, 2 or 3 identicalor different heteroatoms or heteroatom-containing groups as ringmembers, said heteroatoms and heteroatom-containing groups, selectedfrom N, O, S, SO and SO₂. The hetaryl group may be attached to theremainder of the molecule via a ring carbon or via a ring nitrogen.Examples of 5- or 6-membered aromatic heterocyclic rings (also calledheteroaromatic rings or hetaryl) are 2-furyl, 3-furyl, 2-thienyl,3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl,5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl and 2-pyrazinyl. Examples of 8-, 9- or 10-memberedaromatic heterobicyclic rings are hetaryl having one of theaforementioned 5- or 6-membered heteroaromatic rings and anotheraromatic carbocycle or 5- or 6-membered heterocycle fused thereto, forexample a fused benzene, thiophen-, furan-, pyrrol-, pyrazol-,imidazol-, pyridin- or pyrimidin-ring. These bicyclic hetarylenescomprises e.g. quinolinyl, isoquinolinyl, cinnolinyl, indolyl,indolizinyl, isoindolyl, indazolyl, benzofuryl, in particular2-benzofuryl, benzothienyl, in particular 2-benzothienyl,benzo[b]thiazolyl, in particular 2-benzo[b]thiazolyl, benzoxazolyl, inparticular 2-benzoxazolyl, benzothiazolyl, in particular2-benzothiazolyl, benzimidazolyl, in particular 2-benzimidazolyl,imidazo[1,2-a]pyridin-2-yl, thieno[3,2-b]pyridin-5yl,imidazo-[2,1-b]-thiazol-6-yl and 1,2,4-triazolo[1,5-a]pyridin-2-yl.

When # appears in a formula, showing a preferred substructure of acompound of the present invention, it denotes the bond to the rest ofthe molecule.

Cerium Compounds of the Formulae (I.1) and (I)

The compound of formula (I.1)

Ce⁴⁺(L₁L₂L₃L₄)⁴⁻(I.1), wherein

L₁; L₂; L₃; and L₄ are defined above and below, encompasses compounds,wherein

-   -   all four ligands L₁, L₂, L₃ and L₄ have the same meanings,    -   three of the four ligands have the same meanings,    -   two of the four ligands have the same meanings,    -   all four ligands L₁, L₂, L₃ and L₄ have different meaning.

Preferred are compounds of formula (I.1) wherein L₁, L₂, L₃ and L₄ havethe same meanings.

In the cerium compounds of formula (I.1) L₁, L₂, L₃ and L₄ areindependently from each other selected from bidentate ligands having thegeneral formula (I.2). In the following preferred embodiments of thecompounds (I.1) are directly defined by preferred embodiments of theirbidentate ligands (I.2).

Preferred are compounds of formula (I) and ligands of formula (I.2),wherein R¹ and R² are independently selected from CN, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, haloalkoxy, C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl,NR^(4a)R^(4b) and the group A consisting of A1, A2, A3, A4, A5, A6, A7,A8, A9, A10, A11, A12, A13, A14, A15, A16, A17 A18 and A19

where # denotes the bond to the remaining molecule of formula (I) andligands of formula (I.2),

-   -   R^(A), R^(B), R^(c), R^(D) and R^(E) are independently selected        from hydrogen, CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and        phenyl, which is unsubstituted or substituted by 1, 2 or 3        identical or different radicals selected from C₁-C₄-alkyl and        C₁-C₄-haloalkyl;    -   R^(4a), R^(4b) independently represent hydrogen, C₁-C₆-alkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵⁻;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; and    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵.

Another preferred embodiment are compounds of formula (I) and ligands offormula (I.2), wherein R¹ and R² are independently selected from CN,C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b) and thegroup A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12,A13, A14 and A15, where

-   -   R^(A), R^(B), R^(C), R^(D) and R^(E) are independently selected        from hydrogen, CN, halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   R^(4a), R^(4b) independently represent hydrogen, C₁-C₆-alkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵⁻;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; and    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵.

Irrespective of their occurrence the radicals R^(A), R^(B), R^(C), R^(D)and R^(E) are preferably selected from hydrogen, CN, fluorine, chlorine,C₁-C₄-alkyl, C₁-C₄-fluoroalkyl, C₁-C₄-chloroalkyl and phenyl, which isunsubstituted or substituted by 1, 2 or 3 identical or differentradicals selected from C₁-C₄-haloalkyl.

Particularly preferred, the radicals R^(A), R^(B), R^(C), R^(D) andR^(E) are independently from each other selected from hydrogen, CN,fluorine and chlorine.

In another particular embodiment the radicals R^(A), R^(B), R^(C), R^(D)and R^(E) are independently from each other selected from hydrogen, CN,fluorine, chlorine and phenyl, which is substituted by 1 or 2 identicalor different radicals selected from C₁-C₂-haloalkyl.

Especially preferred, the radicals R^(A), R^(B), R^(C), R^(D) and R^(E)all represent fluorine.

Also especially preferred the radicals R^(A), R^(B), R^(D) and R^(E) arehydrogen and R^(C) is 3,5-di(trifluoromethyl)phenyl.

Preferably in formula (I) and ligands of formula (I.2), R¹ and R² areindependently selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl, A1 and A5

where # denotes the bond to the remaining molecule of formula (I) andligands of formula (I.2), and wherein

R^(A), R^(B), R^(C), R^(D) and R^(E) are independently selected fromhydrogen, CN, fluorine, chlorine, C₁-C₄-alkyl, C₁-C₄-fluoroalkyl,C₁-C₄-chloroalkyl and phenyl, which is unsubstituted or substituted by1, 2 or 3 identical or different radicals selected from C₁-C₄-haloalkyl.

In another preferred embodiment in formula (I) and ligands of formula(I.2) R¹ and R² are independently selected from A16 and A17

where # denotes the bond to the remaining molecule of formula (I) andligands of formula (I.2), and wherein

R^(A), R^(B) and R^(C) are independently selected from hydrogen, CN,fluorine, chlorine, C₁-C₄-alkyl, C₁-C₄-fluoroalkyl andC₁-C₄-chloroalkyl. Preferably R^(A), R^(B) and R^(C) are all hydrogen.

In a preferred embodiment, in formula (I) and ligands of formula (I.2),R¹ and R² are independently selected from A1 and A5

where # denotes the bond to the remaining molecule of formula (I) andligands of formula (I.2), and wherein

R^(A), R^(B), R^(C), R^(D) and R^(E) are independently selected fromhydrogen, CN, fluorine, chlorine, C₁-C₄ alkyl, C₁-C₄-fluoroalkyl,C₁-C₄-chloroalkyl and phenyl, which is unsubstituted or substituted by1, 2 or 3 identical or different radicals selected from C₁-C₄-haloalkyl.

In a particularly preferred embodiment in formula (I) and ligands offormula (I.2) R¹ and R² are independently selected from A1 and A5,wherein R^(A), R^(B), R^(C), R^(D) and R^(E) are independently selectedfrom CN, fluorine and chlorine.

In another particularly preferred embodiment in formula (I) R¹ and R²are independently selected from A1 and A5, wherein R^(A), R^(B), R^(C),R^(D) and R^(E) are independently selected from CN, fluorine andchlorine.

In another preferred embodiment in formula (I) and ligands of formula(I.2), R¹ and R² are independently selected from C₁-C₄-alkyl,C₁-C₄-fluoroalkyl, C₁-C₄-chloroalkyl and A1, wherein R^(A), R^(B),R^(C), R^(D) and R^(E) are independently selected from CN, fluorine andchlorine.

In another preferred embodiment, in formula (I), R¹ and R² areindependently selected from C₁-C₄-alkyl, C₁-C₄-fluoroalkyl,C₁-C₄-chloroalkyl and A1, wherein R^(A), R^(B), R^(c), R^(D) and R^(E)are independently selected from CN, fluorine and chlorine.

In a particular embodiment, in formula (I) and ligands of formula (I.2),Wand R² are independently selected from A1 and A5, wherein R^(A), R^(B),R^(C), R^(D) and R^(E) are fluorine.

In a particular embodiment, in formula (I), R¹ and R² are independentlyselected from A1 and A5, wherein R^(A), R^(B), R^(C), R^(D) and R^(E)are fluorine.

In another preferred embodiment in formula (I) and ligands of formula(I.2), R¹ and R² are′A1, wherein R^(A), R^(B), R^(D) and R^(E) arehydrogen and R^(C) is 3,5-di(trifluoromethyl)phenyl.

In another preferred embodiment, in formula (I), R¹ and R² are A1,wherein R^(A), R^(B), R^(D) and R^(E) are hydrogen and R^(C) is3,5-di(trifluoromethyl)phenyl.

Preferred are compounds of formula (I) and ligands of formula (I.2),wherein Y represents the radical CR³ and R³ is selected from hydrogen,CN, nitro, halogen, CF₃ and the group B consisting B1, B2, B3, B4, B5,B6, B7, B8, B9, B10, B11, B12, B13, B14 and B15

where # denotes the bond to the remaining molecule of formula (I) andligands of formula (I.2),

R^(F), R^(G), R^(H), R^(I) and R^(J) are independently selected fromhydrogen, CN, halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl; and

R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₁-C₁₄-aryl,wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5identical or different radicals R⁵.

Irrespective of their occurrence the radicals R^(F), R^(G), R^(H), R^(I)and R^(J) are preferably selected from hydrogen, CN, fluorine, chlorine,C₁-C₄-alkyl, C₁-C₄-fluoroalkyl and C₁-C₄-chloroalkyl.

In a preferred embodiment the radicals R^(A), R^(B), R^(C), R^(D) andR^(E) represent independently CN, fluorine or chlorine.

In formula (I) and ligands of formula (I.2), Y preferably represents aradical CR³, wherein R³ is selected from hydrogen, CN, nitro, halogenCF₃ and B1

where # denotes the bond to the remaining molecule of formula (I) andligands of formula (I.2), and wherein

R^(F), R^(G), R^(H), R^(I) and R^(J) are independently selected fromhydrogen, CN, fluorine and chlorine.

In formula (I) and ligands of formula (I.2), Y preferably represents aradical CR³, wherein R³ represents B1

where # denotes the bond to the remaining molecule of formula (I) andligands of formula (I.2), and wherein

R^(E), R^(G), R^(H), R^(I) and R^(J) are independently selected from CN,fluorine and chlorine.

In another preferred embodiment, Y represents a radical CR³, wherein R³is selected from hydrogen, CN, nitro, fluorine, chlorine and CF₃.

Irrespective of their occurrence, the radicals R^(4a) und R^(4b) arepreferably selected from hydrogen and C₁-C₄-alkyl.

Irrespective of its occurrence, the radical R⁵ is preferably selectedfrom CN, fluorine, chlorine, C₁-C₄-alkyl und C₁-C₄-haloalkyl.

Irrespective of its occurrence, the radical R⁶ is preferably selectedfrom hydrogen and C₁-C₄-alkyl.

Irrespective of its occurrence, the radical R′ is preferably selectedfrom hydrogen and C₁-C₄-alkyl and C₁-C₄-haloalkyl.

In a preferred first embodiment A, compounds of formula (I) and ligandsof formula (I.2) are preferred, wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in particular fluorine, CN and nitro;    -   R¹ and R² independently from each other represent CN,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), in        particular represents C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Particular preferred are compounds of formula (I), wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in particular fluorine, CN and nitro;    -   R¹ and R² independently from each other represent CN, C₁-C₆        alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), in        particular represents C₁-C₄-alkyl or C₁-C₄-haloalkyl.

In a preferred second embodiment B, compounds of formula (I) and ligandsof formula (I.2) are preferred, wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ represents B1, B2, B3, B4, B5, B6,        B7, B8, B9, B10, B11, B12, B13, B14 or B15, in particular        represents B1;    -   R¹ and R² independently from each other represent CN,        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), in        particular represent C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Particular preferred are compounds of formula (I), wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ represents B1, B2, B3, B4, B5, B6,        B7, B8, B9, B10, B11, B12, B13, B14 or B15, in particular        represents B1;    -   R¹ and R² independently from each other represent CN,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), in        particular represent C₁-C₄-alkyl or C₁-C₄-haloalkyl.

In a preferred third embodiment C, compounds of formula (I) and ligandsof formula (I.2) are preferred, wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ represents B1, B2, B3, B4, B5, B6,        B7, B8, B9, B10, B11, B12, B13, B14 or B15, in particular        represents B1;    -   R¹ and R² independently from each other represent A1, A2, A3,        A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 or A15, in        particular represent A1 or A5.

Particular preferred are compounds of formula (I), wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ represents B1, B2, B3, B4, B5, B6,        B7, B8, B9, B10, B11, B12, B13, B14 or B15, in particular        represents B1;    -   R¹ and R² independently from each other represent A1, A2, A3,        A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 or A15, in        particular represent A1 or A5.

In a preferred fourth embodiment D, compounds of formula (I) and ligandsof formula (I.2) are preferred, wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in particular fluorine, CN and nitro;    -   R¹ and R² independently from each other represent A1, A2, A3,        A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 or A15, in        particular represent A1 or A5.

Particular preferred are compounds of formula (I), wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in particular fluorine, CN and nitro;    -   R¹ and R² independently from each other represent A1, A2, A3,        A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 or A15, in        particular represent A1 or A5.

In a preferred fifth embodiment E, compounds of formula (I) and ligandsof formula (I.2) are preferred, wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in particular fluorine, CN and nitro;    -   R¹ represents A1;    -   R² represents CN, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl,        NR^(4a)R^(4b), in particular represents C₁-C₄-alkyl or        C₁-C₄-haloalkyl.

Particular preferred are compounds of formula (I), wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in particular fluorine, CN and nitro;    -   R¹ represents A1;    -   R² represents CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), in        particular represents C₁-C₄-alkyl or C₁-C₄-haloalkyl.

In a preferred sixth embodiment F, compounds of formula (I) and ligandsof formula (I.2) are preferred, wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in hydrogen;    -   R¹ and R² independently from each other represent A16 or A17.

Particular preferred are compounds of formula (I), wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in hydrogen;    -   R¹ and R² independently from each other represent A16 or A17.

In a preferred seventh embodiment G, compounds of formula (I) andligands of formula (I.2) are preferred, wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in hydrogen;    -   R¹ represents A16 or A17;    -   R² represents CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), in        particular represents C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Particular preferred are compounds of formula (I), wherein

-   -   X and W represent S or O, in particular O;    -   Y represents CR³, wherein R³ is selected from hydrogen, CN,        nitro and halogen, in hydrogen;    -   R¹ represents A16 or A17;    -   R² represents CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₅-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), in        particular represents C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Particular preferred are compounds of formula (I.a′)

-   -   Ce⁴⁺[(R¹—C(—O)═C(R³)—C(═O)—R²)(R^(1′)—C(═O))═C(R³)—C(═O)—R²)(R¹″-C(—O)═C(R³″)—C(═O)—R²″)        (R¹″ —C(—O)═C(R³″)—C(═O)—R²″)]⁴⁻(I.a′, wherein    -   (R¹, R², R³), (R^(1′), R^(2′), R^(3′)), (R¹″, R², R³″) and        (R^(1″′), R^(2″′), R^(3″′)) are each selected from the        definition given in one line of the following table 1

TABLE 1 R¹, R^(1′), R^(1′′), R^(1′′′) R², R^(2′), R^(2′′), R^(2′′′) R³,R^(3′), R^(3′′), R^(3′′′) 1. methyl methyl H 2. methyl methyl CN 3.methyl methyl F 4. methyl methyl Cl 5. methyl methyl NO₂ 6. methylmethyl pentafluorophenyl 7. methyl methyl tetrafluoro-2-(trifluoromethyl)phenyl 8. methyl methyl tetrafluoro-3-(trifluoromethyl)phenyl 9. methyl methyl tetrafluoro-4-(trifluoromethyl)phenyl 10. methyl methyl tetrafluoro-2-pyridyl 11.methyl methyl tetrafluoro-3-pyridyl 12. methyl methyltetrafluoro-4-pyridyl 13. methyl methyl tetrafluoro-2-benzonitrile 14.methyl methyl tetrafluoro-3-benzonitrile 15. methyl methyltetrafluoro-4-benzonitrile 16. trifluoromethyl trifluoromethyl H 17.trifluoromethyl trifluoromethyl CN 18. trifluoromethyl trifluoromethyl F19. trifluoromethyl trifluoromethyl Cl 20. trifluoromethyltrifluoromethyl NO₂ 21. trifluoromethyl trifluoromethylpentafluorophenyl 22. trifluoromethyl trifluoromethyl tetrafluoro-2-(trifluoromethyl)phenyl 23. trifluoromethyl trifluoromethyltetrafluoro-3- (trifluoromethyl)phenyl 24. trifluoromethyltrifluoromethyl tetrafluoro-4- (trifluoromethyl)phenyl 25.trifluoromethyl trifluoromethyl tetrafluoro-2-pyridyl 26.trifluoromethyl trifluoromethyl tetrafluoro-3-pyridyl 27.trifluoromethyl trifluoromethyl tetrafluoro-4-pyridyl 28.trifluoromethyl trifluoromethyl tetrafluoro-2-benzonitrile 29.trifluoromethyl trifluoromethyl tetrafluoro-3-benzonitrile 30.trifluoromethyl trifluoromethyl tetrafluoro-4-benzonitrile 31.pentafluoroethyl pentafluoroethyl H 32. pentafluoroethylpentafluoroethyl CN 33. pentafluoroethyl pentafluoroethyl F 34.pentafluoroethyl pentafluoroethyl Cl 35. pentafluoroethylpentafluoroethyl NO₂ 36. pentafluoroethyl pentafluoroethylpentafluorophenyl 37. pentafluoroethyl pentafluoroethyl tetrafluoro-2-(trifluoromethyl)phenyl 38. pentafluoroethyl pentafluoroethyltetrafluoro-3- (trifluoromethyl)phenyl 39. pentafluoroethylpentafluoroethyl tetrafluoro-4- (trifluoromethyl)phenyl 40.pentafluoroethyl pentafluoroethyl tetrafluoro-2-pyridyl 41.pentafluoroethyl pentafluoroethyl tetrafluoro-3-pyridyl 42.pentafluoroethyl pentafluoroethyl tetrafluoro-4-pyridyl 43.pentafluoroethyl pentafluoroethyl tetrafluoro-2-benzonitrile 44.pentafluoroethyl pentafluoroethyl tetrafluoro-3-benzonitrile 45.pentafluoroethyl pentafluoroethyl tetrafluoro-4-benzonitrile 46.heptafluoro-n- heptafluoro-n- H propyl propyl 47. heptafluoro-n-heptafluoro-n- CN propyl propyl 48. heptafluoro-n- heptafluoro-n- Fpropyl propyl 49. heptafluoro-n- heptafluoro-n- Cl propyl propyl 50.heptafluoro-n- heptafluoro-n- NO₂ propyl propyl 51. heptafluoro-n-heptafluoro-n- pentafluorophenyl propyl propyl 52. heptafluoro-n-heptafluoro-n- tetrafluoro-2- propyl propyl (trifluoromethyl)phenyl 53.heptafluoro-n- heptafluoro-n- tetrafluoro-3- propyl propyl(trifluoromethyl)phenyl 54. heptafluoro-n- heptafluoro-n- tetrafluoro-4-propyl propyl (trifluoromethyl)phenyl 55. heptafluoro-n- heptafluoro-n-tetrafluoro-2-pyridyl propyl propyl 56. heptafluoro-n- heptafluoro-n-tetrafluoro-3-pyridyl propyl propyl 57. heptafluoro-n- heptafluoro-n-tetrafluoro-4-pyridyl propyl propyl 58. heptafluoro-n- heptafluoro-n-tetrafluoro-2-benzonitrile propyl propyl 59. heptafluoro-n-heptafluoro-n- tetrafluoro-3-benzonitrile propyl propyl 60.heptafluoro-n- heptafluoro-n- tetrafluoro-4-benzonitrile propyl propyl61. heptafluoro- heptafluoro- H isopropyl isopropyl 62. heptafluoro-heptafluoro- CN isopropyl isopropyl 63. heptafluoro- heptafluoro- Fisopropyl isopropyl 64. heptafluoro- heptafluoro- Cl isopropyl isopropyl65. heptafluoro- heptafluoro- NO₂ isopropyl isopropyl 66. heptafluor-heptafluoro- pentafluorophenyl isopropyl isopropyl 67. heptafluor-heptafluoro- tetrafluoro-2- isopropyl isopropyl (trifluoromethyl)phenyl68. heptafluoro- heptafluoro- tetrafluoro-3- isopropyl isopropyl(trifluoromethyl)phenyl 69. heptafluoro- heptafluoro- tetrafluoro-4-isopropyl isopropyl (trifluoromethyl)phenyl 70. heptafluoro-heptafluoro- tetrafluoro-2-pyridyl isopropyl isopropyl 71. heptafluoro-heptafluoro- tetrafluoro-3-pyridyl isopropyl isopropyl 72. heptafluoro-heptafluoro- tetrafluoro-4-pyridyl isopropyl isopropyl 73. heptafluoro-heptafluoro- tetrafluoro-2-benzonitrile isopropyl isopropyl 74.heptafluoro- heptafluoro- tetrafluoro-3-benzonitrile isopropyl isopropyl75. heptafluoro- heptafluoro- tetrafluoro-4-benzonitrile isopropylisopropyl 76. tert-butyl tert-butyl H 77. tert-butyl tert-butyl CN 78.tert-butyl tert-butyl F 79. tert-butyl tert-butyl Cl 80. tert-butyltert-butyl NO₂ 81. tert-butyl tert-butyl pentafluorophenyl 82.tert-butyl tert-butyl tetrafluoro-2- (trifluoromethyl)phenyl 83.tert-butyl tert-butyl tetrafluoro-3- (trifluoromethyl)phenyl 84.tert-butyl tert-butyl tetrafluoro-4- (trifluoromethyl)phenyl 85.tert-butyl tert-butyl tetrafluoro-2-pyridyl 86. tert-butyl tert-butyltetrafluoro-3-pyridyl 87. tert-butyl tert-butyl tetrafluoro-4-pyridyl88. tert-butyl tert-butyl tetrafluoro-2-benzonitrile 89. tert-butyltert-butyl tetrafluoro-3-benzonitrile 90. tert-butyl tert-butyltetrafluoro-4-benzonitrile 91. nonafluoro-n- nonafluoro-n- H butyl butyl92. nonafluoro-n- nonafluoro-n- CN butyl butyl 93. nonafluoro-n-nonafluoro-n- F butyl butyl 94. nonafluoro-n- nonafluoro-n- Cl butylbutyl 95. nonafluoro-n- nonafluoro-n- NO₂ butyl butyl 96. nonafluoro-n-nonafluoro-n- pentafluorophenyl butyl butyl 97. nonafluoro-n-nonafluoro-n- tetrafluoro-2- butyl butyl (trifluoromethyl)phenyl 98.nonafluoro-n- nonafluoro-n- tetrafluoro-3- butyl butyl(trifluoromethyl)phenyl 99. nonafluoro-n- nonafluoro-n- tetrafluoro-4-butyl butyl (trifluoromethyl)phenyl 100. nonafluoro-n- nonafluoro-n-tetrafluoro-2-pyridyl butyl butyl 101. nonafluoro-n- nonafluoro-n-tetrafluoro-3-pyridyl butyl butyl 102. nonafluoro-n- nonafluoro-n-tetrafluoro-4-pyridyl butyl butyl 103. nonafluoro-n- nonafluoro-n-tetrafluoro-2-benzonitrile butyl butyl 104. nonafluoro-n- nonafluoro-n-tetrafluoro-3-benzonitrile butyl butyl 105. nonafluoro-n- nonafluoro-n-tetrafluoro-4-benzonitrile butyl butyl 106. pentafluorophenylpentafluorophenyl H 107. pentafluorophenyl pentafluorophenyl CN 108.pentafluorophenyl pentafluorophenyl F 109. pentafluorophenylpentafluorophenyl Cl 110. pentafluorophenyl pentafluorophenyl NO₂ 111.pentafluorophenyl pentafluorophenyl pentafluorophenyl 112.pentafluorophenyl pentafluorophenyl tetrafluoro-2-(trifluoromethyl)phenyl 113. pentafluorophenyl pentafluorophenyltetrafluoro-3- (trifluoromethyl)phenyl 114. pentafluorophenylpentafluorophenyl tetrafluoro-4- (trifluoromethyl)phenyl 115.pentafluorophenyl pentafluorophenyl tetrafluoro-2-pyridyl 116.pentafluorophenyl pentafluorophenyl tetrafluoro-3-pyridyl 117.pentafluorophenyl pentafluorophenyl tetrafluoro-4-pyridyl 118.pentafluorophenyl pentafluorophenyl tetrafluoro-2-benzonitrile 119.pentafluorophenyl pentafluorophenyl tetrafluoro-3-benzonitrile 120.pentafluorophenyl pentafluorophenyl tetrafluoro-4-benzonitrile 121.4-pyrimidyl 4-pyrimidyl H 122. 4-pyrimidyl 4-pyrimidyl CN 123.4-pyrimidyl 4-pyrimidyl F 124. 4-pyrimidyl 4-pyrimidyl Cl 125.4-pyrimidyl 4-pyrimidyl NO₂ 126. 4-pyrimidyl 4-pyrimidylpentafluorophenyl 127. 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-(trifluoromethyl)phenyl 128. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-(trifluoromethyl)phenyl 129. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-(trifluoromethyl)phenyl 130. 4-pyrimidyl 4-pyrimidyltetrafluoro-2-pyridyl 131. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl132. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 133. 4-pyrimidyl4-pyrimidyl tetrafluoro-2-benzonitrile 134. 4-pyrimidyl 4-pyrimidyltetrafluoro-3-benzonitrile 135. 4-pyrimidyl 4-pyrimidyltetrafluoro-4-benzonitrile 136. 2-pyrimidyl 2-pyrimidyl H 137.2-pyrimidyl 2-pyrimidyl CN 138. 2-pyrimidyl 2-pyrimidyl F 139.2-pyrimidyl 2-pyrimidyl Cl 140. 2-pyrimidyl 2-pyrimidyl NO₂ 141.2-pyrimidyl 2-pyrimidyl pentafluorophenyl 142. 2-pyrimidyl 2-pyrimidyltetrafluoro-2- (trifluoromethyl)phenyl 143. 2-pyrimidyl 2-pyrimidyltetrafluoro-3- (trifluoromethyl)phenyl 144. 2-pyrimidyl 2-pyrimidyltetrafluoro-4- (trifluoromethyl)phenyl 145. 2-pyrimidyl 2-pyrimidyltetrafluoro-2-pyridyl 146. 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-pyridyl147. 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl 148. 2-pyrimidyl2-pyrimidyl tetrafluoro-2-benzonitrile 149. 2-pyrimidyl 2-pyrimidyltetrafluoro-3-benzonitrile 150. 2-pyrimidyl 2-pyrimidyltetrafluoro-4-benzonitrile 151. 3,5-bis(trifluoro- 3,5-bis(trifluoro- Hmethyl)-phenyl methyl)-phenyl 152. 3,5-bis(trifiuoro- trifluoromethyl Hmethyl)-phenyl 153. phenyl pentafluoroethyl H 154. furan-2-yltrifluoromethyl H 155. furan-2-yl pentafluoroethyl H 156.3,5-bis(trifluoro- pentafluoroethyl H methyl)-phenyl 157.3′,5′-bis(trifluoro- pentafluoroethyl H methyl)-[1,1′- biphenyl]-4-yl158. 3′,5′-bis(trifluoro- trifluoromethyl H methyl)-[1,1′-biphenyl]-4-yl 159. 4-fluoro-3- pentafluoroethyl H trifluoromethyl-phenyl 160. 4-fluoro-3- 3,5-bis(trifluoro- H trifluoromethyl-methyl)-phenyl phenyl 161. 3,4,5-trifluoro- 3,4,5-trifluoro- H phenylphenyl 162. 3,4,5-trifluoro- pentafluoroethyl H phenyl 163.4-(trifluoro- 4-(trifluoro- H methyl)phenyl methyl)phenyl 164.4-(trifluoro- pentafluoroethyl H methyl)phenyl 165.2,4,6-tris(trifluoro- 2,4,6-tris(trifluoro- H methyl)phenylmethyl)phenyl 166. 2,4,6-tris(trifluoro- Pentafluoroethyl Hmethyl)phenyl 167. 3,5-bis(trifluoro- 3,5-bis(trifluoro- CNmethyl)-phenyl methyl)-phenyl 168. 2,4,6-tris(trifluoro-2,4,6-tris(trifluoro- CN methyl)phenyl methyl)phenyl 169.3,5-bis(trifluoro- pentafluoroethyl 3,5-bis(trifluoromethyl)-methyl)-phenyl phenyl 170. 3,4-bis(trifluoro- 3,4-bis(trifluoro- Hmethyl)-phenyl methyl)-phenyl 171. 3,4-bis(trifluoro- trifluoromethyl Hmethyl)-phenyl 172. 3,4-bis(trifluoro- pentafluoroethyl3,5-bis(trifluoromethyl)- methyl)-phenyl phenyl 173. 3,4-bis(trifluoro-pentafluoroethyl H methyl)-phenyl 174. 3,4-bis(trifluoro-3,4-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 175. 4-cyano-3-(tri-3,5-bis(trifluoro- H fluoromethyl)- methyl)-phenyl phenyl 176.4-cyano-3-(tri- pentafluoroethyl H fluoromethyl)- phenyl 177.3,5-bis(trifluoro- pentafluoroethyl CN methyl)-phenyl 178. 4-cyano-2,6-4-cyano-2,6- H bis(trifluoro- bis(trifluoro- methyl)-phenylmethyl)-phenyl 179. 4-cyano-2,6- pentafluoroethyl H bis(trifluoro-methyl)-phenyl 180. 2,4-bis(trifluoro- 2,6-bis(trifluoro- Hmethyl)-phenyl methyl)-phenyl 181. 2,4-bis(trifluoro- 2,6-bis(trifluoro-CN methyl)-phenyl methyl)-phenyl 182. 4-(3′,5′-bis pentafluoroethyl H(trifluoromethyl) phenyl)-2,6- bis(trifluoro- methyl)-phenyl 183. phenylphenyl CN 184. 3,5-bis(trifluoro- 3,5-bis(trifluoro- CF₃ methyl)-phenylmethyl)-phenyl 185. 3,5-bis(trifluoro- trifluoromethyl CF3methyl)-phenyl 186. phenyl pentafluoroethyl CF₃ 187. 3,5-bis(trifluoro-pentafluoroethyl CF₃ methyl)-phenyl 188. 3,4,5-trifluoro-3,4,5-trifluoro- CF₃ phenyl phenyl 189. 4-(trifluoro- 4-(trifluoro- CF₃methyl)phenyl methyl)phenyl 190. phenyl phenyl CF₃

Particularly preferred are the compounds of formula (I.a)

wherein R¹, R² and R³ are as defined in table 2:

TABLE 2 R¹ R² R³ 1. methyl methyl H 2. methyl methyl CN 3. methyl methylF 4. methyl methyl Cl 5. methyl methyl NO₂ 6. methyl methylpentafluorophenyl 7. methyl methyl tetrafluoro-2-(trifluoromethyl)phenyl 8. methyl methyl tetrafluoro-3-(trifluoromethyl)phenyl 9. methyl methyl tetrafluoro-4-(trifluoromethyl)phenyl 10. methyl methyl tetrafluoro-2-pyridyl 11.methyl methyl tetrafluoro-3-pyridyl 12. methyl methyltetrafluoro-4-pyridyl 13. methyl methyl tetrafluoro-2-benzonitrile 14.methyl methyl tetrafluoro-3-benzonitrile 15. methyl methyltetrafluoro-4-benzonitrile 16. trifluoromethyl trifluoromethyl H 17.trifluoromethyl trifluoromethyl CN 18. trifluoromethyl trifluoromethyl F19. trifluoromethyl trifluoromethyl Cl 20. trifluoromethyltrifluoromethyl NO₂ 21. trifluoromethyl trifluoromethylpentafluorophenyl 22. trifluoromethyl trifluoromethyl tetrafluoro-2-(trifluoromethyl)phenyl 23. trifluoromethyl trifluoromethyltetrafluoro-3- (trifluoromethyl)phenyl 24. trifluoromethyltrifluoromethyl tetrafluoro-4- (trifluoromethyl)phenyl 25.trifluoromethyl trifluoromethyl tetrafluoro-2-pyridyl 26.trifluoromethyl trifluoromethyl tetrafluoro-3-pyridyl 27.trifluoromethyl trifluoromethyl tetrafluoro-4-pyridyl 28.trifluoromethyl trifluoromethyl tetrafluoro-2-benzonitrile 29.trifluoromethyl trifluoromethyl tetrafluoro-3-benzonitrile 30.trifluoromethyl trifluoromethyl tetrafluoro-4-benzonitrile 31.pentafluoroethyl pentafluoroethyl H 32. pentafluoroethylpentafluoroethyl CN 33. pentafluoroethyl pentafluoroethyl F 34.pentafluoroethyl pentafluoroethyl Cl 35. pentafluoroethylpentafluoroethyl NO₂ 36. pentafluoroethyl pentafluoroethylpentafluorophenyl 37. pentafluoroethyl pentafluoroethyl tetrafluoro-2-(trifluoromethyl)phenyl 38. pentafluoroethyl pentafluoroethyltetrafluoro-3- (trifluoromethyl)phenyl 39. pentafluoroethylpentafluoroethyl tetrafluoro-4- (trifluoromethyl)phenyl 40.pentafluoroethyl pentafluoroethyl tetrafluoro-2-pyridyl 41.pentafluoroethyl pentafluoroethyl tetrafluoro-3-pyridyl 42.pentafluoroethyl pentafluoroethyl tetrafluoro-4-pyridyl 43.pentafluoroethyl pentafluoroethyl tetrafluoro-2-benzonitrile 44.pentafluoroethyl pentafluoroethyl tetrafluoro-3-benzonitrile 45.pentafluoroethyl pentafluoroethyl tetrafluoro-4-benzonitrile 46.heptafluoro-n-propyl heptafluoro-n- H propyl 47. heptafluoro-n-propylheptafluoro-n- CN propyl 48. heptafluoro-n-propyl heptafluoro-n- Fpropyl 49. heptafluoro-n-propyl heptafluoro-n- Cl propyl 50.heptafluoro-n-propyl heptafluoro-n- NO₂ propyl 51. heptafluoro-n-propylheptafluoro-n- pentafluorophenyl propyl 52. heptafluoro-n-propylheptafluoro-n- tetrafluoro-2- propyl (trifluoromethyl)phenyl 53.heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3- propyl(trifluoromethyl)phenyl 54. heptafluoro-n-propyl heptafluoro-n-tetrafluoro-4- propyl (trifluoromethyl)phenyl 55. heptafluoro-n-propylheptafluoro-n- tetrafluoro-2-pyridyl propyl 56. heptafluoro-n-propylheptafluoro-n- tetrafluoro-3-pyridyl propyl 57. heptafluoro-n-propylheptafluoro-n- tetrafluoro-4-pyridyl propyl 58. heptafluoro-n-propylheptafluoro-n- tetrafluoro-2-benzonitrile propyl 59.heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-benzonitrile propyl60. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-benzonitrilepropyl 61. heptafluoro- heptafluoro- H isopropyl isopropyl 62.heptafluoro- heptafluoro- CN isopropyl isopropyl 63. heptafluoro-heptafluoro- F isopropyl isopropyl 64. heptafluoro- heptafluoro- Clisopropyl isopropyl 65. heptafluoro- heptafluoro- NO₂ isopropylisopropyl 66. heptafluoro- heptafluoro- pentafluorophenyl isopropylisopropyl 67. heptafluoro- heptafluoro- tetrafluoro-2- isopropylisopropyl (trifluoromethyl)phenyl 68. heptafluoro- heptafluoro-tetrafluoro-3- isopropyl isopropyl (trifluoromethyl)phenyl 69.heptafluoro- heptafluoro- tetrafluoro-4- isopropyl isopropyl(trifluormethyl)phenyl 70. heptafluoro- heptafluoro-tetrafluoro-2-pyridyl isopropyl isopropyl 71. heptafluoro- heptafluoro-tetrafluoro-3-pyridyl isopropyl isopropyl 72. heptafluoro- heptafluoro-tetrafluoro-4-pyridyl isopropyl isopropyl 73. heptafluoro- heptafluoro-tetrafluoro-2-benzonitrile isopropyl isopropyl 74. heptafluoro-heptafluoro- tetrafluoro-3-benzonitrile isopropyl isopropyl 75.heptafluoro- heptafluoro- tetrafluoro-4-benzonitrile isopropyl isopropyl76. tert-butyl tert-butyl H 77. tert-butyl tert-butyl CN 78. tert-butyltert-butyl F 79. tert-butyl tert-butyl Cl 80. tert-butyl tert-butyl NO₂81. tert-butyl tert-butyl pentafluorophenyl 82. tert-butyl tert-butyltetrafluoro-2- (trifluoromethyl)phenyl 83. tert-butyl tert-butyltetrafluoro-3- (trifluoromethyl)phenyl 84. tert-butyl tert-butyltetrafluoro-4- (trifluoromethyl)phenyl 85. tert-butyl tert-butyltetrafluoro-2-pyridyl 86. tert-butyl tert-butyl tetrafluoro-3-pyridyl87. tert-butyl tert-butyl tetrafluoro-4-pyridyl 88. tert-butyltert-butyl tetrafluoro-2-benzonitrile 89. tert-butyl tert-butyltetrafluoro-3-benzonitrile 90. tert-butyl tert-butyltetrafluoro-4-benzonitrile 91. nonafluoro-n-butyl nonafluoro-n- H butyl92. nonafluoro-n-butyl nonafluoro-n- CN butyl 93. nonafluoro-n-butylnonafluoro-n- F butyl 94. nonafluoro-n-butyl nonafluoro-n- Cl butyl 95.nonafluoro-n-butyl nonafluoro-n- NO₂ butyl 96. nonafluoro-n-butylnonafluoro-n- pentafluorophenyl butyl 97. nonafluoro-n-butylnonafluoro-n- tetrafluoro-2- butyl (trifluoromethyl)phenyl 98.nonafluoro-n-butyl nonafluoro-n- tetrafluoro-3- butyl(trifluormethyl)phenyl 99. nonafluoro-n-butyl nonafluoro-n-tetrafluoro-4- butyl (trifluoromethyl)phenyl 100. nonafluoro-n-butylnonafluoro-n- tetrafluoro-2-pyridyl butyl 101. nonafluoro-n-butylnonafluoro-n- tetrafluoro-3-pyridyl butyl 102. nonafluoro-n-butylnonafluoro-n- tetrafluoro-4-pyridyl butyl 103. nonafluoro-n-butylnonafluoro-n- tetrafluoro-2-benzonitrile butyl 104. nonafluoro-n-butylnonafluoro-n- tetrafluoro-3-benzonitrile butyl 105. nonafluoro-n-butylnonafluoro-n- tetrafluoro-4-benzonitrile butyl 106. pentafluorophenylpentafluoro- H phenyl 107. pentafluorophenyl pentafluoro- CN phenyl 108.pentafluorophenyl pentafluoro- F phenyl 109. pentafluorophenylpentafluoro- Cl phenyl 110. pentafluorophenyl pentafluoro- NO₂ phenyl111. pentafluorophenyl pentafluoro- pentafluorophenyl phenyl 112.pentafluorophenyl pentafluoro- tetrafluoro-2- phenyl(trifluoromethyl)phenyl 113. pentafluorophenyl pentafluoro-tetrafluoro-3- phenyl (trifluoromethyl)phenyl 114. pentafluorophenylpentafluoro- tetrafluoro-4- phenyl (trifluoromethyl)phenyl 115.pentafluorophenyl pentafluoro- tetrafluoro-2-pyridyl phenyl 116.pentafluorophenyl pentafluoro- tetrafluoro-3-pyridyl phenyl 117.pentafluorophenyl pentafluoro- tetrafluoro-4-pyridyl phenyl 118.pentafluorophenyl pentafluoro- tetrafluoro-2-benzonitrile phenyl 119.pentafluorophenyl pentafluoro- tetrafluoro-3-benzonitrile phenyl 120.pentafluorophenyl pentafluoro- tetrafluoro-4-benzonitrile phenyl 121.4-pyrimidyl 4-pyrimidyl H 122. 4-pyrimidyl 4-pyrimidyl CN 123.4-pyrimidyl 4-pyrimidyl F 124. 4-pyrimidyl 4-pyrimidyl Cl 125.4-pyrimidyl 4-pyrimidyl NO₂ 126. 4-pyrimidyl 4-pyrimidylpentafluorophenyl 127. 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-(trifluoromethyl)phenyl 128. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-(trifluoromethyl)phenyl 129. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-(trifluoromethyl)phenyl 130. 4-pyrimidyl 4-pyrimidyltetrafluoro-2-pyridyl 131. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl132. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 133. 4-pyrimidyl4-pyrimidyl tetrafluoro-2-benzonitrile 134. 4-pyrimidyl 4-pyrimidyltetrafluoro-3-benzonitrile 135. 4-pyrimidyl 4-pyrimidyltetrafluoro-4-benzonitrile 136. 2-pyrimidyl 2-pyrimidyl H 137.2-pyrimidyl 2-pyrimidyl CN 138. 2-pyrimidyl 2-pyrimidyl F 139.2-pyrimidyl 2-pyrimidyl Cl 140. 2-pyrimidyl 2-pyrimidyl NO₂ 141.2-pyrimidyl 2-pyrimidyl pentafluorophenyl 142. 2-pyrimidyl 2-pyrimidyltetrafluoro-2- (trifluoromethyl)phenyl 143. 2-pyrimidyl 2-pyrimidyltetrafluoro-3- (trifluoromethyl)phenyl 144. 2-pyrimidyl 2-pyrimidyltetrafluoro-4- (trifluoromethyl)phenyl 145. 2-pyrimidyl 2-pyrimidyltetrafluoro-2-pyridyl 146. 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-pyridyl147. 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl 148. 2-pyrimidyl2-pyrimidyl tetrafluoro-2-benzonitrile 149. 2-pyrimidyl 2-pyrimidyltetrafluoro-3-benzonitrile 150. 2-pyrimidyl 2-pyrimidyltetrafluoro-4-benzonitrile 151. 3,5-bis(trifluoro- 3,5-bis(trifluoro- Hmethyl)-phenyl methyl)-phenyl 152. 3,5-bis(trifluoro- trifluoromethyl Hmethyl)-phenyl 153. phenyl pentafluoroethyl H 154. furan-2-yltrifluoromethyl H 155. furan-2-yl pentafluoroethyl H 156.3,5-bis(trifluoro- pentafluoroethyl H methyl)-phenyl 157.3′,5′-bis(trifluoro- pentafluoroethyl H methyl)-[1,1′- biphenyl]-4-yl158. 3′,5′-bis(trifluoro- trifluoromethyl H methyl)-[1,1′-biphenyl]-4-yl 159. 4-fluoro-3-trifluoro- pentafluoroethyl Hmethyl-phenyl 160. 4-fluoro-3-trifluoro- 3,5-bis(trifluoro- Hmethyl-phenyl methyl)-phenyl 161. 3,4,5-trifluorophenyl 3,4,5-trifluoro-H phenyl 162. 3,4,5-trifluorophenyl pentafluoroethyl H 163.4-(trifluoro- 4-(trifluoro- H methyl)phenyl methyl)phenyl 164.4-(trifluoro- pentafluoroethyl H methyl)phenyl 165.2,4,6-tris(trifluoro- 2,4,6-tris(trifluoro- H methyl)phenylmethyl)phenyl 166. 2,4,6-tris(trifluoro- Pentafluoroethyl Hmethyl)phenyl 167. 3,5-bis(trifluoro- 3,5-bis(trifluoro- CNmethyl)-phenyl methyl)-phenyl 168. 2,4,6-tris(trifluoro-2,4,6-tris(trifluoro- CN methyl)phenyl methyl)phenyl 169.3,5-bis(trifluoro- pentafluoroethyl 3,5-bis(trifluoromethyl)-methyl)-phenyl phenyl 170. 3,4-bis(trifluoro- 3,4-bis(trifluoro- Hmethyl)-phenyl methyl)-phenyl 171. 3,4-bis(trifluoro- trifluoromethyl Hmethyl)-phenyl 172. 3,4-bis(trifluoro- pentafluoroethyl3,5-bis(trifluoromethyl)- methyl)-phenyl phenyl 173. 3,4-bis(trifluoro-pentafluoroethyl H methyl)-phenyl 174. 3,4-bis(trifluoro-3,4-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 175.4-cyano-3-(trifluoro- 3,5-bis(trifluoro- H methyl)-phenyl methyl)-phenyl176. 4-cyano-3-(trifluoro- pentafluoroethyl H methyl)-phenyl 177.3,5-bis(trifluoro- pentafluoroethyl CN methyl)-phenyl 178.4-cyano-2,6-bis(tri- 4-cyano-2,6- H fluoromethyl)- bis(trifluoro- phenylmethyl)-phenyl 179. 4-cyano-2,6-bis(tri- pentafluoroethyl Hfluoromethyl)- phenyl 180. 2,4-bis(trifluoro- 2,6-bis(trifluoro- Hmethyl)-phenyl methyl)-phenyl 181. 2,4-bis(trifluoro- 2,6-bis(trifluoro-CN methyl)-phenyl methyl)-phenyl 182. 4-(3′,5′-bis(trifluoro-pentafluoroethyl H methyl)phenyl)-2,6- bis(trifluoromethyl)- phenyl 183.phenyl phenyl CN 184. 3,5-bis(trifluoro- 3,5-bis(trifluoro- CF₃methyl)-phenyl methyl)-phenyl 185. 3,5-bis(trifluoro- trifluoromethylCF₃ methyl)-phenyl 186. phenyl pentafluoroethyl CF₃ 187.3,5-bis(trifluoro- pentafluoroethyl CF₃ methyl)-phenyl 188. 3,4,5-3,4,5- CF₃ trifluorophenyl trifluorophenyl 189. 4-(trifluoro-4-(trifluoro- CF₃ methyl)phenyl methyl)phenyl 190. phenyl phenyl CF₃

Especially preferred are the compounds of formula (I.a), wherein R¹, R²and R³ are as defined in table 3:

TABLE 3 R¹ R² R³ 191. pentafluorophenyl pentafluorophenyl H 192. phenylphenyl CN 193. tert-butyl tert-butyl H 194. tert-butyl tert-butyl CN195. 3,5-bis(trifluoro- 3,5-bis(trifluoro- H methyl)-phenylmethyl)-phenyl 196. 3,5-bis(trifluoro- trifluoromethyl H methyl)-phenyl197. phenyl pentafluoroethyl H 198. furan-2-yl trifluoromethyl H 199.furan-2-yl pentafluoroethyl H 200. 3,5-bis(trifluoro- pentafluoroethyl Hmethyl)-phenyl 201. 3′,5′-bis(trifluoro- pentafluoroethyl Hmethyl)-[1,1′- biphenyl]-4-yl 202. 3′,5′-bis(trifluoro- trifluoromethylH methyl)-[1,1′- biphenyl]-4-yl 203. 4-fluoro-3-trifluoro-pentafluoroethyl H methyl-phenyl 204. 4-fluoro-3-trifluoro-3,5-bis(trifluoro- H methyl-phenyl methyl)-phenyl 205.3,4,5-trifluorophenyl 3,4,5-trifluoro- H phenyl 206.3,4,5-trifluorophenyl pentafluoroethyl H 207. 4-(trifluoro-4-(trifluoro- H methyl)phenyl methyl)phenyl 208. 4-(trifluoro-pentafluoroethyl H methyl)phenyl 209. 2,4,6-tris(trifluoro-2,4,6-tris(trifluoro- H methyl)phenyl methyl)phenyl 210.2,4,6-tris(trifluoro- Pentafluoroethyl H methyl)phenyl 211.3,5-bis(trifluoro- 3,5-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl212. 2,4,6-tris(trifluoro- 2,4,6-tris(trifluoro- CN methyl)phenylmethyl)phenyl 213. 3,5-bis(trifluoro- pentafluoroethyl3,5-bis(trifluoromethyl)- methyl)-phenyl phenyl 214. 3,4-bis(trifluoro-3,4-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 215.3,4-bis(trifluoro- trifluoromethyl H methyl)-phenyl 216.3,4-bis(trifluoro- pentafluoroethyl 3,5-bis(trifluoromethyl)-methyl)-phenyl phenyl 217. 3,4-bis(trifluoro- pentafluoroethyl Hmethyl)-phenyl 218. 3,4-bis(trifluoro- 3,4-bis(trifluoro- CNmethyl)-phenyl methyl)-phenyl 219. 4-cyano-3-(trifluoro-3,5-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 220.4-cyano-3-(trifluoro- pentafluoroethyl H methyl)-phenyl 221.3,5-bis(trifluoro- pentafluoroethyl CN methyl)-phenyl 222.4-cyano-2,6-bis(tri- 4-cyano-2,6- H fluoromethyl)- bis(trifluoro- phenylmethyl)-phenyl 223. 4-cyano-2,6-bis(tri- pentafluoroethyl Hfluoromethyl)- phenyl 224. 2,4-bis(trifluoro- 2,6-bis(trifluoro- Hmethyl)-phenyl methyl)-phenyl 225. 2,4-bis(trifluoro- 2,6-bis(trifluoro-CN methyl)-phenyl methyl)-phenyl 226. 4-(3′,5′-bis(trifluoro-pentafluoroethyl H methyl)phenyl)-2,6- bis(trifluoromethyl)- phenyl

In formula (I.a) the four ligands L₂, L₃ and L₄ bound to the cerium atomhave the same meanings.

The homoleptic compounds of formulae (I.1) and (I) are produced byreacting the β-diketone ligand with a ceric salt. Usually the ceric saltis soluble in the reaction medium. Suitable salts are ceric ammoniumnitrate and ceric ammonium sulphate. The β-diketone ligands are eithercommercial available or they can be prepared by a synthesis known to askilled person.

The heteroleptic compounds of formula (I.1) are produced by

-   -   mixing two different homoleptic cerium compounds in a suitable        solvent,    -   mixing a homoleptic cerium compound with a ligand or its        alkaline/earth alkaline salt different from the ligands of the        compound,    -   vapor deposition of two different homoleptic cerium compounds,    -   vapor deposition (vapor co-condensation) of homoleptic cerium        compounds with a ligand different from the ligands of the        compound.

Component

In the context of the invention, an electronic component is understoodto be a discrete or integrated electrical component, which uses theproperties of compounds of the general formula (I.1) or (I) orsemiconductor matrix materials containing a compound of the generalformula (I.1) or (I). In a special embodiment, the electronic componenthas a layer structure comprising in particular 2, 3, 4, 5, 6, 7 or morelayers, wherein at least one of the layers contains at least onecompound of the general formula (I.1) or (I). In particular, theelectronic component has a layer structure comprising in particular 2,3, 4, 5, 6, 7 or more layers, wherein at least one of the layerscontains at least one compound of the general formula (I). Each of thelayers may also contain inorganic materials, or the component may alsocomprise layers, which are composed entirely from inorganic materials.

Preferably, the electronic component is selected from organic fieldeffect transistors (OFETs), organic electroluminescent devices, organicsolar cells (OSCs), devices for electrophotography, organic opticaldetectors, organic photoreceptors, light-emitting electrochemical cells(LECs) and organic laser diodes. Organic field effect transistors(OFETs) are preferably organic thin film transistors (OTFTs). Organicelectroluminescent devices are preferably organic light-emitting diodes(OLEDs). Organic solar cells are preferably exciton solar cells, dyesensitized solar cells (DSSCs) or perovskite solar cells. Devices forelectrophotography are preferably photoconductive materials in organicphotoconductors (OPC).

Preferably, the electronic component according to the invention is inthe form of an organic light-emitting diode, an organic solar cell, aphotovoltaic cell, an organic diode or an organic transistor, preferablya field effect transistor or thin-film transistor or a Perovskite solarcell.

The electronic component may be preferably an organicelectro-luminescent device, in particular in the form of an organiclight-emitting diode (OLED). An organic electroluminescent devicecomprises a cathode, an anode and at least one emitting layer. Inaddition to these layers, it may also comprise other layers, e.g. one ormore hole injection layers, hole transport layers, hole blocking layers,electron transport layers, electron injection layers, exciton blockinglayers, electron blocking layers and/or charge generation layers.Intermediate layers, which have e.g. an exciton-blocking-function canalso be inserted between two emitting layers. Not all of these layersmust necessarily be present.

A preferred embodiment is an electronic component, in particular in theform of an OLED, wherein the layer comprising the compound of formula(I.1) or (I) is a hole transport layer or a hole injection layer.Especially, the electronic component, in particular in the form of anOLED, wherein the layer comprising the compound of formula (I) is a holetransport layer, a hole injection layer or an electron blocking layer.Generally, a hole injection layer is a layer which facilitates electroninjection from the anode into the organic semiconductor matrix material.The hole injection layer can be placed directly adjacent to the anode. Ahole transport layer transports the holes from the anode to the emittinglayer and is located between a hole injection layer and an emittinglayer.

A preferred embodiment is an electronic component in the form of anorganic solar cell. Generally organic solar cells are layered andusually comprises at least the following layers: anode, at least onephotoactive layer and cathode. These layers are generally applied to asubstrate commonly used for this purpose. The photoactive region of thesolar cell may comprise two layers, each of which has a homogeneouscomposition and forms a flat donor-acceptor heterojunction. Aphotoactive region can also comprise a mixed layer and form adonor-acceptor heterojunction in the form of a donor-acceptor bulkheterojunction. In addition to these layers, the organic solar cell canalso comprises other layers, e.g. selected from

-   -   Layers with electron transport layer properties (electron        transport layer, ETL),    -   Layers comprising a hole-conducting material (hole transport        layer, HTL), these do not have to absorb radiation,    -   Exciton and hole blocking layers (e.g. EBLs), these must not        absorb, and    -   Multiplier layers.

Another preferred embodiment is an electronic component in the form ofan organic solar cell, wherein the layer, which comprises the compoundof formula (I.1) or (I), has electron conductivity properties (electrontransport layer, ETL). Especially, the electronic component is in theform of an organic solar cell, wherein the layer, which comprises thecompound of formula (I), has electron conductivity properties (electrontransport layer, ETL).

A special embodiment is an electronic component, especially in the formof an organic solar cell, wherein the layer, which comprises at leastone of the compounds of formula (I.1) or (I) is part of a pn-junctionconnecting a light absorbing unit to an additional light absorbing unitin a tandem device or in a multi-stacked device and/or a pn-junctionconnecting a cathode or an anode to a light absorbing unit. Inparticular, the electronic component is in the form of an organic solarcell, wherein the layer which comprises at least one of the compounds offormula (I) is part of a pn-junction connecting a light absorbing unitto an additional light absorbing unit in a tandem device or in amulti-stacked device and/or a pn-junction connecting a cathode or ananode to a light absorbing unit.

Semiconductor Matrix Materials

The compounds of formula (I.1) or (I) according to the invention andused according to the invention, as well as their charge transfercomplexes, their reduction products, can be used as doping agents inorganic semiconductor matrix materials, in particular as p-dopant inhole transport layers. The doped semiconductor matrix material,preferably comprising at least one electron donor and at least onecompound of the formula (I.1) or (I), as defined above. The electrondonor is preferably selected from4,4′,4″-tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine (2-TNATA),4,4′,4″-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine (m-MTDATA),N,N,N′,N′-tetrakis(4-methoxy-phenyl)benzidine (MeO-TPD),(2,2′,7,7′-tetrakis-(N,N-diphenylamino)-9,9′-spiro-bifluorene(spiro-TTB), N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-benzidine,N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-9,9-spiro-bifluorene,9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene,2,2′-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spiro-bifluorene,N,N′-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1-biphenyl]-4-yl)-[1,1′-biphenyl]-4-amine)(BPAPF), N,N′-bis(phenanthren-9-yl)-N,N′-bis(phenyl)-benzidine,1,3,5-tris{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene,tri(terphenyl-4-yl)amine, diaminoterphenylene,diaminotrimethylphenylindanes,N,N′-bis(9,9-dimethylfluoren-2-yl)-N,N′-diphenyl-benzidine (BF-DPB),N,N′-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1-biphenyl]-4-yl)-[1,1-biphenyl]-4-amine)(BPAPF),N4,N4,N4′,N4′-tetrakis(9,9-dimethyl-9H-fluoren-2-yl)-[1,1-biphenyl]-4,4′-diamine(TDMFB),N-([1,1′-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine,(2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluorene](spiro-MeO-TPD),N([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amineand mixtures thereof.

Suitable diaminoterphenyls are described in DE 102012007795.Diaminotrimethylphenylindanes are described in WO 2018/206769.

In particular, the electron donors are selected from4,4′,4″-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNATA),4,4′,4″-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine (m-MTDATA),N,N,N′,N′-tetrakis(4-methoxy-phenyl)benzidine (MeO-TPD),(2,2′,7,7′-tetrakis-(N,N-diphenylamino)-9,9′-spirobifluorene(spiro-TTB), N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-benzidine,N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-9,9-spiro-bifluorene,9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene,2,2′-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spiro-bifluorene,N,N′-((9H-fluoren-9,9-diyl)bis(4,1-phenylen))bis(N-([1,1-biphenyl]-4-yl)-[1,1-biphenyl]-4-amine)(BPAPF), N,N′-bis(phenanthren-9-yl)-N,N′-bis(phenyl)-benzidine,1,3,5-tris{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene,tri(terphenyl-4-yl)amine,N-(4-(6-((9,9-dimethyl-9H-fluoren-2-yl)(6-methoxy-[1,1-biphenyl]-3-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(6-methoxy-[1,1-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine,phenyl]-4-yl)-N-(4-(6-([1,1′-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine,N,N′-di([1,1′-biphenyl]-4-yl)-3-(4-(di([1,1′-biphenyl]-4-yl)amino)phenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine,N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine,N-(4-(6-(9,9′-spirobi[fluoren]-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine,N-(4-(6-(dibenzo[b,d]furan-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-2-amine,9-(4-(6-(9H-carbazol-9-yl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9H-carbazole,N-([1,1-biphenyl]-4-yl)-3-(4-([1,1-biphenyl]-4-yl(4-methoxyphenyl)amino)phenyl)-N-(4-methoxyphenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine,3-(4-(bis(6-methoxy-[1,1′-biphenyl]-3-yl)amino)phenyl)N,N-bis(6-methoxy-[1,1-biphenyl]-3-yl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine,N1-([1,1′-biphenyl]-4-yl)-N1-(4-(6-([1,1-biphenyl]-4-yl(4-(diphenylamino)phenyl)amino)1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N4,N4-diphenylbenzene-1,4-diamine,N,N-di([1,1′-biphenyl]-4-yl)-4′-(6-(4-(di([1,1′-biphenyl]-4-yl)amino)phenyl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)-[1,1′-biphenyl]-4-amine,N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine,N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine,N,N′-bis(9,9-dimethyl-fluoren-2-yl)N,N′-diphenyl-benzidine (BF-DPB),N,N′-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4-amine)(BPAPF),N4,N4,N4′,N4′-tetrakis(9,9-dimethyl-9H-fluoren-2-yl)1,1′-biphenyl]-4,4′-diamine(TDMFB),N-([1,1′-biphenyl]-2-yl)-N(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine,(2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluorene](spiro-MeO-TPD),a mixture ofN-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amineandN-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine,N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amineand mixtures thereof.

Of course, other suitable organic semiconductor matrix materials,especially hole-conducting materials with semiconducting properties, canalso be used.

Doping

The doping can take place in particular in such a manner that the molarratio of matrix molecule to compounds of formula (I.1) or (I) is 10000:1 to 1:1, preferably 1000: 1 to 2: 1, especially 5:1 to 100: 1. Inparticular, the doping can take place in particular in such a mannerthat the molar ratio of matrix molecule to compounds of formula (I) is10000:1 to 1:1, preferably 1000:1 to 2:1, especially 5:1 to 100: 1.

Preparation of the Doped Semiconductor Matrix Material

The doping of the particular matrix material (in the following alsoindicated as hole-conducting matrix HT) with the compounds of thegeneral formula (I.1) or (I) according to the invention and usedaccording to the invention can be produced by one or a combination ofthe following processes:

-   -   a) Mixed evaporation in the vacuum with a source for HT and a        source for at least one compound of the general formula (I.1)        and (I) in particular at least one compound of the general        formula (I).    -   b) Sequential deposition of HT and at least one compound of the        general formula (I.1) or (I), in particular at least one        compound of the general formula (I), with subsequent inward        diffusion of the doping agent by thermal treatment.    -   c) Doping of an HT layer by a solution of at least one compound        of the general formula (I.1) or (I), in particular at least one        compound of the general formula (I), with subsequent evaporation        of the solvent by thermal treatment.    -   d) Surface doping of an HT layer by a layer of at least one        compound of the general formula (I.1) or (I), in particular at        least one compound of the general formula (I), applied on either        or both surfaces of the HT layer.    -   e) Preparation of a solution of host and at least one compound        of the general formula (I.1) or (I), in particular at least one        compound of the general formula (I), and forming a film from the        solution e.g. by coating, casting or printing techniques or        other film preparing techniques known to a person skilled in the        art.

Another object of the invention is the use of a compound (I.1) or amixture thereof or the use of a compound (I) or a mixture thereof, inparticular the use of a compound (I) or a mixture thereof as definedabove

-   -   as organic semiconductor,    -   as doping agent in organic semiconductor matrix materials,        especially as p-dopant in hole transport layers,    -   as electron transport material,    -   as charge injector in a charge injection layer,    -   as cathode material in organic batteries,    -   as electrochromic material.

A further object of the invention is the use of Ce(III) complex anionsobtained by reduction of a compound (I.1) or (I) as defined above or ofcharge transfer complexes of a compound (I.1) or (I) as defined abovewith electron donors as organic conductor or as electrochromic material.

A further object of the invention are compounds of the general formula(I.1)

Ce⁴⁺(L₁L₂L₃L₄)⁴⁻  (I.1),

and mixtures thereof, wherein

L₁; L₂; L₃; and L₄ are independently from each other a bidentate ligandhaving the general formula (I.2)

wherein

-   -   X and W independently from each other represent O, S or NR⁶;    -   Y represents N or CR³⁻;

R¹, R² independently from each other represent CN, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfanyl,C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), C₆-C₁₄-aryl or hetaryl having 4to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or differentheteroatoms or heteroatom-containing groups as ring members, selectedfrom N, NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl areunsubstituted or substituted by 1, 2, 3, 4 or 5 identical or differentradicals R⁸⁻;

-   -   R³ represents hydrogen, CN, nitro, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻;    -   R^(4a)R^(4b) independently from each other represent hydrogen,        C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵⁻;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   R⁶ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻;    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵⁻,    -   R⁸ represents CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or        C₆-C₁₄-aryl, which is unsubstituted or substituted by 1, 2 or 3        identical or different radicals selected from C₁-C₄-alkyl and        C₁-C₄-haloalkyl;

with the proviso that the following compounds are excluded:

A further object of the invention are compounds of the general formula(I)

and their charge transfer complexes, their reduction products andmixtures thereof, wherein

-   -   X and W independently from each other represent 0, S or NR⁶;    -   Y represents N or CR³;    -   R¹, R² independently from each other represent CN, C₁-C₆ alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁸⁻;    -   R³ represents hydrogen, CN, nitro, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b),        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻;    -   R^(4a)R^(4b) independently from each other represent hydrogen,        C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted or        substituted by 1, 2, 3, 4 or 5 identical or different radicals        R⁵⁻;    -   R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   R⁶ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₆-C₁₄-aryl or hetaryl having 4 to 13 carbon atoms, wherein        hetaryl has 1, 2 or 3 identical or different heteroatoms or        heteroatom-containing groups as ring members, selected from N,        NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl are        unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or        different radicals R⁵⁻,    -   R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or        C₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1,        2, 3, 4 or 5 identical or different radicals R⁵⁻;    -   R⁸ represents CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or        C₆-C₁₄-aryl, which is unsubstituted or substituted by 1, 2 or 3        identical or different radicals selected from C₁-C₄-alkyl and        C₁-C₄-haloalkyl;

with the proviso that the following compounds are excluded:

The following examples illustrate the invention without limiting it inany way.

Examples

Synthesis of 1:

1,3-bis(perfluorophenyl)propane-1,3-dione was prepared according toliterature (R. Filler et al., J. Org. Chem. 35(4), 1970, 930).

1,3-Bis(perfluorophenyl)propane-1,3-dione (1.61 g, 4.00 mmol) wasdissolved in ethanol (50 ml) and 1M NaOH in ethanol (4 ml, 4 mmol) wasadded. The solution was stirred for 5 minutes, then ceric (IV) ammoniumnitrate (0.55 g, 1 mmol) was added. The dark red solution was stirredfor 2 hours. The volatiles were removed in vacuo and the residuesuspended in hexane (40 ml). After refluxing for 10 min, the suspensionwas filtered while hot and the filtrate was allowed to cool to roomtemperature. Dark red crystals were isolated by vacuum filtration anddried under vacuum. The solid was recrystallized from hexane filteredand dried (0.77 g, 0.43 mmol, 44% yield).

¹H NMR (300 MHz, CDCl₃) δ 6.09.

¹⁹F NMR (282 MHz, CDCl₃) δ-139.25, −139.31, −149.63, −149.70, −149.78,−160.69, −160.70, 160.73, −160.78, −160.80, −160.85, −160.88, −160.89.

Melting point: 183° C.

Cyclovoltametry in dichloromethane showed the following:

E _(1/2)(vs.Fc/Fc ⁺)=+0,13V

Cyclovoltametry in acetonitrile showed the following:

E _(1/2)(vs.Fc/Fc ⁺)=+0,1V

Preparation of the samples:

A substrate (laboratory glass 1×1 cm) was cleaned with acetone, ethanoland isopropanol in an ultrasonic bath.

The following solutions/concentrations were used for solvent processing:

-   -   1. spiro-MeO-TAD        (N2,N2,N2′,N2′,N7,N7,N7′,N7′-octakis(4-methoxyphenyl)-9,9′-spirobi[9H-fluoren]-2,2′,7,7′-tetramine)        in chlorobenzene: 30 mg/ml    -   2. Dopant 1 and Spiro-MeO-TAD and in chlorbenzene: 3 mg/ml        (dopant 1) and 30 mg/ml Spiro-MeO-TAD

A spincoater from Sawatec AG, Switzerland, was used for the applicationof the layers. For this purpose, the substrate surface was wetted withsolution (a drop was placed in the middle of the substrate). The spincoating was carried out for 60 seconds at 1000 rpm with closed lid andopen ventilation slits. Subsequently, gold metal contacts were depositedby evaporation in a vacuum (10-7 mbar) (30 nm, 1 Å/s).

Conductivity Spiro-MeG-TAD without dopant: <1·10⁻⁹ S/cm

Conductivity Spiro-MeG-TAD with 10 wt % 1 as dopant: 8.4·10⁻⁵ S/cm

The compound has been solution processed together with the holetransport material CAS [1364603-07-5]. At a doping concentration of 4mol % a conductivity of 2.6·10⁻⁶ S/cm has been achieved.

Synthesis of 2:

Compound 2 is commercially available and was sublimated withoutdecomposition. The sublimation temperature T_(Tsubl) was 130 to 140° C.(pressure; 2·10⁻⁶ mbar).

Synthesis of 3:

2-Benzoyl-3-oxo-3-phenylpropanenitrile was prepared according toliterature (Lava R. Kadel, John R. Kromer, Curtis E. Moore, David M.Eichhorn Polyhedron 125, 2017, 206-218.).

2-Benzoyl-3-oxo-3-phenylpropanenitrile (0,50 g, 2 mmol) was dissolved inethanol (15 ml), and 1M NaOH in ethanol (2 ml, 2 mmol) was added. Thesolution was stirred for 5 minutes, then ceric(IV) ammonium nitrate(0,27 g, 0.5 mmol) dissolved in ethanol (5 ml) was added. The dark redsolution was stirred for 15 min and after that filtered. The dark solidwas washed with water (100 ml) and ethanol (10 ml) and dried. 460 mg ofa dark red solid were obtained.

Cyclovoltametry in dichloromethane showed the following potential:

E ^(1/2)(vs.Fc/Fc ⁺)=+0,03V

Synthesis of 4:

4,4-Dimethyl-3-oxo-2-pivaloylpentanenitrile was prepared according toliterature (C. M. Silvernail et al., Polyhedron 20, 2001, 3113.).

4,4-Dimethyl-3-oxo-2-pivaloylpentanenitril (0,84 g, 4 mmol) wasdissolved in ethanol (30 ml), and 1M NaOH in ethanol (4 ml, 4 mmol) wasadded. The solution was stirred for 5 minutes, then ceric(IV) ammoniumnitrate (0,55 g, 1 mmol) dissolved in ethanol (10 ml) was added. Thedark red solution was stirred for 15 min. The solvent was removed invacuo. The residue was extracted with diethylether (50 ml) and filtered.The solvent of the filtrate was removed under vacuum. Dark red solid,500 mg, 51% yield.

Compound 4 was sublimated. A dark red solid was obtained. Thesublimation temperature T_(subl) was 160° C. (pressure; 2·10⁻⁶ mbar).

Cyclovoltametry in dichloromethane showed the following potential:

E _(1/2)(vs.Fc/Fc ⁺)=−0,08V

Synthesis of 5

Diisopropylamine (3 g, 30 mmol) was dissolved in 25 mL dry toluene. Thesolution was cooled to 0° C. and n-BuLi (n-butyllithium, 1.6M in hexane,19 mL, 30 mmol) was added. After 10 min,3′,5′-Bis(trifluoromethyl)acetophenone (7.68 g, 30 mmol) was added.After 1 min, 3′,5′ bis(trifluoromethyl)benzoyl chloride (5.5 g, 20 mmol)was added and the cooling bath was removed. After 2 min, acetic acidconc. (10 mL) was added followed by 20 mL of water and 10 mL of toluene.The two phases were separated, the organic phase was dried over MgSO₄and rotated off under reduced pressure. The crude diketone wasrecrystallized from hexane (yield of1,3-bis(3,5-bis(trifluoromethyl)phenyl)propane-1,3-dione 3.2 g, 6.45mmol, 33%).

1,3-bis(3,5-bis(trifluoromethyl)phenyl)propane-1,3-dione (2.57 g, 5.18mmol) was dissolved in ethanol (100 ml) and 1M NaOH in ethanol (5.2 ml,5.2 mmol) was added. The solution was stirred for 5 minutes, then asolution of ceric ammonium nitrate (0.71 g, 1.3 mmol) in ethanol (40 ml)was added. The dark red solution was stirred for 15 min and filtered.The volatiles were removed in vacuo and the residue was redissolved indichloromethane (DCM, 300 ml) and washed with water (100 ml). Theorganic phase was then dried over MgSO₄ and concentrated under reducedpressure. Hexane (400 mL) was added to yield purple crystals, which werefiltered and dried under vacuum (2.5 g, 1.17 mmol, 90% yield).

Melting point: 237° C. (onset) at 10 K/min, determined with DSC

Cyclovoltametry in acetonitrile showed the following potential:

E _(1/2)(vs.Fc/Fc ⁺(MeCN):=−0.04V

The compound 5 was co-evaporated with the hole transport materialspiro-MeO-TPD(2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluoren]. At adoping concentration of 3 mol % a conductivity of 8.2·10⁻⁵ S/cm has beenachieved.

The compound was co-evaporated with the hole transport material MeO-TPD(N,N,N′,N′-tetrakis(4-methoxy-phenyl)benzidine). At a dopingconcentration of 3 mol % a conductivity of 5.2·10⁻⁵ S/cm has beenachieved.

Synthesis of 6

1-(3,5-bis(trifluoromethyl)phenyl)-4,4,4-trifluorobutane-1,3-dione wasprepared according to literature (Liu et al., Molecules 2016, 21, 828.).

1-(3,5-bis(trifluoromethyl)phenyl)-4,4,4-trifluorobutane-1,3-dione (2 g,5.68 mmol) was dissolved in ethanol (50 ml) and 1M NaOH in ethanol (5.6ml, 5.6 mmol) was added. The solution was stirred for 5 minutes, then asolution of ceric (IV) ammonium nitrate (0.78 g, 1.42 mmol) in ethanol(20 ml) was added. The dark red solution was stirred for 15 min andfiltered. The volatiles were removed in vacuo and the residueredissolved in dichloromethane (300 ml), washed with water (100 ml). Theorganic phase was then dried over MgSO₄ and concentrated under reducedpressure. Hexane (50 mL) was added to the mixture and the latter wasstored at −20° C. overnight. The isolated solid was then recrystallizedfrom hot hexane (1 g, 0.64 mmol, 45%).

Melting point: 155° C. (peak) at 10 K/min determined with DSCCyclovoltametry in acetonitrile showed the following potential:

E _(1/2)(vs.Fc/Fc ⁺(MeCN):=+0.35V

The compound 6 was co-evaporated with the hole transport material BF-DPB(N,N′-bis(9,9-dimethyl-fluoren-2-yl)-N,N′-diphenyl-benzidine). With adoping concentration of 6 mol % a conductivity of 7.2·10⁻⁶ S/cm has beenachieved.

The compound was co-evaporated with the hole transport material MeO-TPD.

With a doping concentration of 9 mol % a conductivity of 1.6·10⁻⁴ S/cmhas been achieved.

The compound was co-evaporated with the hole transport material BPAPF.

With a doping concentration of 13 mol % a conductivity of 3·10⁻⁵ S/cmhas been achieved.

Synthesis of 7

4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione is commercialavailable.

4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione (1.8 g, 8.1 mmol) wasdissolved in ethanol (40 ml) and 1M NaOH in ethanol (8.1 ml, 8.1 mmol)was added. The solution was stirred for 5 minutes, then a solution ofceric (IV) ammonium nitrate (1.11 g, 2 mmol) in ethanol (20 ml) wasadded. The dark red precipitate was stirred for 15 min and filtered.

The solid was rinsed with water (100 ml). The latter was redissolved indichloromethane (400 ml) and washed with water (2×200 ml). The organicphase was then dried over MgSO₄ and concentrated under reduced pressure.Hexane (300 mL) was added to yield purple crystals, which were filtered,rinsed with hexane (50 ml), pentane (50 ml) and dried under vacuum (1.5g, 1.46 mmol, 73% yield).

Melting point: 209° C. (peak) at 10 K/min determined with DSCCyclovoltametry in acetonitrile showed the following potential:

E _(1/2)(vs.Fc/Fc ⁺(MeCN):=+0.20V

Synthesis of 8

4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione is commercial available.

4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione (1.57 g, 7.6 mmol) wasdissolved in ethanol (40 ml) and 1M NaOH in ethanol (7.6 ml, 7.6 mmol)was added. The solution was stirred for 5 minutes, then a solution ofceric (IV) ammonium nitrate (1.04 g, 1.9 mmol) in ethanol (20 ml) wasadded. The dark red precipitate was stirred for 15 min and filtered. Thesolid was rinsed with water (100 ml). The latter was redissolved indichloromethane (300 ml) and washed with water (100 ml). The organicphase was then dried over MgSO₄ and concentrated under reduced pressure.Hexane (200 mL) was added to yield to purple crystals, which werefiltered, rinsed with pentane (100 ml) and dried under vacuum (yield:1.2 g, 1.32 mmol, 66%).

Melting point: 166° C. (peak) at 10 K/min determined with DSC.

Cyclovoltametry in acetonitrile showed the following potential:

E _(1/2)(vs.Fc/Fc ⁺(MeCN):=+0.24V

Synthesis of 9

3′,5′ Bis(trifluoromethyl)acetophenone (4.32 g, 16.9 mmol) and ethyl2,2,3,3,3-pentafluoropropanoate (4.86 g, 25.3 mmol) were dissolved indry methanol (100 ml). MeONa (1.82, 33.8 mmol) in methanol (10 ml) wasadded and the mixture was refluxed for 2 hours. The resulting solutionswas evaporated under reduced pressure. The crude was redissolved inEtOAc (100 ml) and HCl (6 M, 50 ml) was added. The organic phase wasseparated, dried over MgSO₄ and rotated off. The red oily diketone waspurified by vacuum distillation yielding to a pale yellow oil of1-(3,5-bis(trifluoromethyl)phenyl)4,4,5,5,5-pentafluoropentane-1,3-dione(yield: 4.8 g, 12 mmol, 71%).

1-(3,5-Bis(trifluoromethyl)phenyl)-4,4,5,5,5-pentafluoropentane-1,3-dione(2.22 g, 5.52 mmol) was dissolved in ethanol (50 ml) and 1M NaOH inethanol (5.5 ml, 5.5 mmol) was added. The solution was stirred for 5minutes, then a solution of ceric ammonium nitrate (0.76 g, 1.38 mmol)in ethanol (15 ml) was added. The dark red solution was stirred for 15min and filtered. The solution was evaporated under reduced pressure.The red oil was extracted with hexane (10 ml) and crystallized uponstanding overnight at room temperature. The isolated solid wasrecrystallized from hot hexane and stored at −20° C. (yield 2.02 g, 1.16mmol, 84%).

Melting point: 129° C. (peak) at 10 K/min determined with DSCCyclovoltametry in acetonitrile showed the following potential:

E _(1/2)(vs.Fc/Fc ⁺(MeCN):=+0.46V

Synthesis of 10

1-(3′,5′-Bis(trifluoromethyl)-[1,1-biphenyl]-4-yl)ethan-1-one (4 g, 12mmol) was dissolved in THF (50 mL). The mixture was cooled to 0° C. andNaH (1.44 g, 60 mmol) was added.

The reaction mixture was stirred for 20 min, then ethyl2,2,3,3,3-pentafluoropropanoate (6.9 g, 36 mmol) was added. The coldbath was removed and the mixture was stirred overnight. The solution wasconcentrated under reduced pressure, water (20 mL) was added followed byHCl (6M, 15 mL). The mixture was extracted with ethyl acetate (300 mL).The organic phase was washed with water (50 mL) and brine (50 mL), driedover MgSO₄ and rotated off. The crude material was purified byfiltration over silica (DCM as eluent), yielding a pale red solid of1-(3′,5′-bis(trifluoromethyl)-[1,1-biphenyl]-4-yl)-4,4,4-trifluorobutane-1,3-dione(yield: 3.2 g, 62%).1-(3′,5′-bis(trifluoromethyl)-[1,1-biphenyl]-4-yl)-4,4,5,5,5-pentafluoropentane-1,3-dione(1.52 g, 3.17 mmol) was dissolved in ethanol (50 ml) and 1M NaOH inethanol (3.2 ml, 3.2 mmol) was added. The solution was stirred for 5minutes, then a solution of ceric (IV) ammonium nitrate (0.43 g, 0.79mmol) in ethanol (20 ml) was added. The dark red solution was stirredfor 15 min and filtered. The volatiles were removed in vacuo and theresidue was redissolved in DCM (250 ml) and washed with water (100 ml).The organic phase was dried over MgSO₄ and rotated off under reducedpressure. The mixture was redissolved in DCM (50 mL) and hexane (200 mL)was added. The solution was concentrated under reduced pressure andstored at −20° C. yielding dark red crystals, which were filtered anddried under vacuum (yield 0.6 g, 0.3 mmol, 37%).

Melting point: 214° C. (peak) at 10 K/min determined with DSC

Cyclovoltametry in acetonitrile showed the following potential:

E _(1/2)(vs.Fc/Fc ⁺:=+0.43V

Synthesis of 11

Methyl 4-cyano-3-(trifluoromethyl)benzoate (2.09 g, 9.12 mmol) wasdissolved in THF (50 mL). The mixture was cooled to 0° C. and NaH (706mg, 29.4 mmol) was added. The reaction mixture was stirred for 20 min,then 1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-one (1.95 g, 7.6 mmol)was added. The cold bath was removed and the mixture was stirredovernight. The solution was concentrated under reduced pressure, water(10 mL) was added followed by HCl (6M, 10 mL). The mixture was extractedwith ethyl acetate (40 mL). The organic phase was washed with water (50mL) and brine (50 mL), dried over MgSO₄ and rotated off. The crudematerial was purified recrystallization from hot EtOH, yielding acolorless microcrystalline solid (1.32 g, 39%).

Complex:

4-(3-(3,5-bis(trifluoromethyl)phenyl)-3-oxopropanoyl)-2-(trifluoromethyl)benzonitrile(1.32 g, 2.91 mmol) was dissolved in EtOH (50 ml) and 1M NaOH in EtOH(2.9 ml, 2.9 mmol) was added. The solution was stirred for 5 minutes,then a solution of ceric ammonium nitrate (0.4 g, 0.73 mmol) in EtOH (20ml) was added. The dark red solution was stirred for 15 min andconcentrated under reduced pressure. The dark red precipitate wasfiltered and rinsed with water (50 mL), EtOH (5 mL) and hexanes (15 mL).The isolated solid was dried under vacuum (1.06 g, 1.16 mmol, 75%).

Potential measured in acetonitrile+0,10V vs. Fc/Fc⁺.

Synthesis of 12 (Mixture of Homoleptic and Heteroleptic Cer-Complexes)

A mixture of the ligands L¹ (1.00 g) and L² (1.02 g) with the molarratio of 1:1) has been dissolved in 10 ml of EtOH. 9.2 ml of a1M-solution of NaOH in EtOH was added in one portion while stirring.1.26 g of ceric ammonium nitrate (CAN) dissolved in 10 ml of EtOH wereadded dropwise. The red precipitated was filtered off and washed twotimes with water. After drying the red powder was analyzed by massspectrometry (Atmospheric Pressure Chemical Ionization APCI-, AdvionASAP Mass Spectrometer). The mass spectrum indicated formation of thetwo homoleptic complexes Ce(L¹)₄ and Ce(L²)₄ as well as all possibleheteroleptic complexes as depicted above.

Synthesis of 13: (Heteroleptic Cer-Complex)

52 mg of ligand salt NaL³ were dissolved in 10 ml EtOH and 216 mg of thecomplex Ce(L²)₄ were added. To the resulting suspension, 5 ml of THFwere added and a homogeneous red solution was formed. Mass spectrometricanalysis (Atmospheric Pressure Chemical Ionization APCI-, Advion ASAPMass Spectrometer) of that solution showed partial formation of the newcomplex Ce(L²)₃L³.

1. An electronic component comprising hole transport layer and/or a holeinjection layer, which comprises at least one compound of the generalformula (I.1)Ce⁴⁺(L₁L₂L₃L₄)⁴⁻  (I.1) or mixtures thereof, wherein L₁; L₂; L₃; and L₄are independently from each other selected from a bidentate ligandhaving the general formula (I.2)

wherein X and W independently from each other represent O, S or NR⁶⁻; Yrepresents N or CR³⁻; R¹, R² independently from each other represent CN,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), C₆-C₁₄-arylor hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3identical or different heteroatoms or heteroatom-containing groups asring members, selected from N, NR⁷, O, S, SO and SO₂, wherein aryl andhetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical ordifferent radicals R⁸⁻; R³ represents hydrogen, CN, nitro, halogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C_(€)-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), C₆-C₁₄-arylor hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3identical or different heteroatoms or heteroatom-containing groups asring members, selected from N, NR⁷, O, S, SO and SO₂, wherein aryl andhetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical ordifferent radicals R⁵⁻; R^(4a)R^(4b) independently from each otherrepresent hydrogen, C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl isunsubstituted or substituted by 1, 2, 3, 4 or 5 identical or differentradicals R⁵⁻; R⁵ represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;R⁶ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₆-C₁₄-aryl orhetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3identical or different heteroatoms or heteroatom-containing groups asring members, selected from N, NR⁷, O, S, SO and SO₂, wherein aryl andhetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical ordifferent radicals R⁵⁻; R⁷ represents hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted orsubstituted by 1, 2, 3, 4 or 5 identical or different radicals R⁵⁻; R⁸represents CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₆-C₁₄-aryl,which is unsubstituted or substituted by 1, 2 or 3 identical ordifferent radicals selected from C₁-C₄-alkyl and C₁-C₄-haloalkyl.
 2. Theelectronic component according to claim 1 comprising hole transportlayer and/or a hole injection layer, which comprises at least onecompound of the general formula (I)

or mixtures thereof, wherein X and W independently from each otherrepresent O, S or NR⁶⁻; Y represents N or CR³⁻; R¹, R² independentlyfrom each other represent CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfanyl,C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), C₆-C₁₄-aryl or hetaryl having 4to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or differentheteroatoms or heteroatom-containing groups as ring members, selectedfrom N, NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl areunsubstituted or substituted by 1, 2, 3, 4 or 5 identical or differentradicals R⁸⁻; R³ represents hydrogen, CN, nitro, halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆ -alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfanyl,C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b), C₆-C₁₄-aryl or hetaryl having 4to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or differentheteroatoms or heteroatom-containing groups as ring members, selectedfrom N, NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl areunsubstituted or substituted by 1, 2, 3, 4 or 5 identical or differentradicals R⁵⁻; R^(4a)R^(4b) independently from each other representhydrogen, C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted orsubstituted by 1, 2, 3, 4 or 5 identical or different radicals R⁵⁻; R⁵represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; R⁶ representshydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₆-C₁₄-aryl or hetaryl having 4to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or differentheteroatoms or heteroatom-containing groups as ring members, selectedfrom N, NR⁷, O, S, SO and SO₂, wherein aryl and hetaryl areunsubstituted or substituted by 1, 2, 3, 4 or 5 identical or differentradicals R⁵⁻; R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl orC₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4or 5 identical or different radicals R⁵⁻; R⁸ represents CN, halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₆-C₁₄-aryl, which is unsubstituted orsubstituted by 1, 2 or 3 identical or different radicals selected fromC₁-C₄-alkyl and C₁-C₄-haloalkyl.
 3. The electronic component accordingto claim 1, wherein R¹ and R² in ligands of formula (I.2) areindependently selected from CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfanyl,C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b) and the group A consisting of A1,A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17,A18 and A19

where # denotes the bond to the remaining molecule of formula (I.2) and(I), R^(A), R^(B), R^(C), R^(D) and R^(E) are independently selectedfrom hydrogen, CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and phenyl,which is unsubstituted or substituted by 1, 2 or 3 identical ordifferent radicals selected from C₁-C₄-alkyl and C₁-C₄-haloalkyl;R^(4a), R^(4b) independently represent hydrogen, C₁-C₆-alkyl orC₆-C₁₄-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4or 5 identical or different radicals R⁵⁻; R⁵ represents CN, halogen,C₁-C₄-alkyl or C₁-C₄-haloalkyl; and R⁷ represents hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted orsubstituted by 1, 2, 3, 4 or 5 identical or different radicals R⁵⁻. 4.The electronic component according to claim 3, wherein in A1, A2, A3,A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 and A15 the radicalsR^(A), R^(B), R^(C), R^(D) and R^(E) are independently from anotherselected from hydrogen, CN, fluorine, chlorine, C₁-C₄-alkyl,C₁-C₄-fluoroalkyl, C₁-C₄-chloroalkyl and phenyl, which is unsubstitutedor substituted by 1, 2 or 3 identical or different radicals selectedfrom C₁-C₄-haloalkyl.
 5. The electronic component according claim 1,wherein in ligands of formula (I.2) Y represents the radical CR³,wherein R³ is selected from hydrogen, CN, nitro, halogen, CF₃ and thegroup B consisting B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12,B13, B14 and B15

where # denotes the bond to the remaining molecule of formula (I.2),R^(E), R^(G), R^(H), R^(I) and R^(J) are independently selected fromhydrogen, CN, halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl; and R⁷represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₁-C₁₄-aryl,wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5identical or different radicals R⁵.
 6. The electronic componentaccording to claim 1, wherein in ligands of formula (I.2) R¹ and R² areindependently selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl, A1, A5, A16and A17

where # denotes the bond to the remaining molecule of formula (I.2), andwherein R^(A), R^(B), R^(C), R^(D) and R^(E) are independently selectedfrom hydrogen, CN, fluorine, chlorine, C₁-C₄-alkyl, C₁-C₄-fluoroalkyl,C₁-C₄-chloroalkyl and phenyl, which is unsubstituted or substituted by1, 2 or 3 identical or different radicals selected from C₁-C₄-haloalkyl.7. The electronic component according to claim 1, wherein in ligands offormula (I.2) Y represents a radical CR³ and wherein R³ is selected fromhydrogen, CN, nitro, halogen, CF₃ and B1

where # denotes the bond to the remaining molecule of formulae (I.2) and(I), and wherein R^(E), R^(G), R^(H), R^(I) and R^(J) are independentlyselected from hydrogen, CN, fluorine and chlorine.
 8. The electroniccomponent according to claim 1, wherein the compounds of formula (I.1)are selected from compounds of formula (I.a′)Ce⁴⁺[(R¹—C(—O)═C(R³)—C(═O)—R²)(R¹—C(—O)═C(R^(3′))—C(═O)—R^(2′))(R¹—C(—O)═C(R³″)—C(═O)—R²″)(R¹″′—C(—O)═C(R^(3′)″)— C(═O)—R^(2′)″)]⁴⁻(I.a′), wherein (R¹, R², R³),(R^(1′), R^(2′), R^(3′)), (R¹″, R²″, R³″) and (R^(1′)″, R^(2′)″,R^(3′)″) are each selected from the definition given in one line of thefollowing table R¹, R^(1′), R^(1′′), R^(1′′′) R², R^(2′), R^(2′′),R^(2′′′) R³, R^(3′), R^(3′′), R^(3′′′) methyl methyl H methyl methyl CNmethyl methyl F methyl methyl Cl methyl methyl NO₂ methyl methylpentafluorophenyl methyl methyl tetrafluoro-2- (trifluoromethyl)phenylmethyl methyl tetrafluoro-3- (trifluoromethyl)phenyl methyl methyltetrafluoro-4- (trifluoromethyl)phenyl methyl methyltetrafluoro-2-pyridyl methyl methyl tetrafluoro-3-pyridyl methyl methyltetrafluoro-4-pyridyl methyl methyl tetrafluoro-2-benzonitrile methylmethyl tetrafluoro-3-benzonitrile methyl methyltetrafluoro-4-benzonitrile trifluoromethyl trifluoromethyl Htrifluoromethyl trifluoromethyl CN trifluoromethyl trifluoromethyl Ftrifluoromethyl trifluoromethyl Cl trifluoromethyl trifluoromethyl NO₂trifluoromethyl trifluoromethyl pentafluorophenyl trifluoromethyltrifluoromethyl tetrafluoro-2- (trifluoromethyl)phenyl trifluoromethyltrifluoromethyl tetrafluoro-3- (trifluoromethyl)phenyl trifluoromethyltrifluoromethyl tetrafluoro-4- (trifluoromethyl)phenyl trifluoromethyltrifluoromethyl tetrafluoro-2-pyridyl trifluoromethyl trifluoromethyltetrafluoro-3-pyridyl trifluoromethyl trifluoromethyltetrafluoro-4-pyridyl trifluoromethyl trifluoromethyltetrafluoro-2-benzonitrile trifluoromethyl trifluoromethyltetrafluoro-3-benzonitrile trifluoromethyl trifluoromethyltetrafluoro-4-benzonitrile pentafluoroethyl pentafluoroethyl Hpentafluoroethyl pentafluoroethyl CN pentafluoroethyl pentafluoroethyl Fpentafluoroethyl pentafluoroethyl Cl pentafluoroethyl pentafluoroethylNO₂ pentafluoroethyl pentafluoroethyl pentafluorophenyl pentafluoroethylpentafluoroethyl tetrafluoro-2- (trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-3- (trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-4- (trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-2-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-3-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-4-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-2-benzonitrile pentafluoroethyl pentafluoroethyltetrafluoro-3-benzonitrile pentafluoroethyl pentafluoroethyltetrafluoro-4-benzonitrile heptafluoro-n-propyl heptafluoro-n- H propylheptafluoro-n-propyl heptafluoro-n- CN propyl heptafluoro-n-propylheptafluoro-n- F propyl heptafluoro-n-propyl heptafluoro-n- Cl propylheptafluoro-n-propyl heptafluoro-n- NO₂ propyl heptafluoro-n-propylheptafluoro-n- pentafluorophenyl propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-2- propyl (trifluoromethyl)phenylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-3- propyl(trifluoromethyl)phenyl heptafluoro-n-propyl heptafluoro-n-tetrafluoro-4- propyl (trifluoromethyl)phenyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-2-pyridyl propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-3-pyridyl propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-4-pyridyl propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-2-benzonitrile propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-3-benzonitrile propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-4-benzonitrile propyl heptafluoro-isopropylheptafluoro- H isopropyl heptafluoro-isopropyl heptafluoro- CN isopropylheptafluoro-isopropyl heptafluoro- F isopropyl heptafluoro-isopropylheptafluoro- Cl isopropyl heptafluoro-isopropyl heptafluoro- NO₂isopropyl heptafluor-iso-propyl heptafluoro- pentafluorophenyl isopropylheptafluor-iso-propyl heptafluoro- tetrafluoro-2- isopropyl(trifluoromethyl)phenyl heptafluoro-isopropyl heptafluoro-tetrafluoro-3- isopropyl (trifluoromethyl)phenyl heptafluoro-isopropylheptafluoro- tetrafluoro-4- isopropyl (trifluoromethyl)phenylheptafluoro-isopropyl heptafluoro- tetrafluoro-2-pyridyl isopropylheptafluoro-isopropyl heptafluoro- tetrafluoro-3-pyridyl isopropylheptafluoro-isopropyl heptafluoro- tetrafluoro-4-pyridyl isopropylheptafluoro-isopropyl heptafluoro- tetrafluoro-2-benzonitrile isopropylheptafluoro-isopropyl heptafluoro- tetrafluoro-3-benzonitrile isopropylheptafluoro-isopropyl heptafluoro- tetrafluoro-4-benzonitrile isopropyltert-butyl tert-butyl H tert-butyl tert-butyl CN tert-butyl tert-butyl Ftert-butyl tert-butyl Cl tert-butyl tert-butyl NO₂ tert-butyl tert-butylpentafluorophenyl tert-butyl tert-butyl tetrafluoro-2-(trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-3-(trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-4-(trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-2-pyridyltert-butyl tert-butyl tetrafluoro-3-pyridyl tert-butyl tert-butyltetrafluoro-4-pyridyl tert-butyl tert-butyl tetrafluoro-2-benzonitriletert-butyl tert-butyl tetrafluoro-3-benzonitrile tert-butyl tert-butyltetrafluoro-4-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl Hnonafluoro-n-butyl nonafluoro-n-butyl CN nonafluoro-n-butylnonafluoro-n-butyl F nonafluoro-n-butyl nonafluoro-n-butyl Clnonafluoro-n-butyl nonafluoro-n-butyl NO₂ nonafluoro-n-butylnonafluoro-n-butyl pentafluorophenyl nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-2- (trifluoromethyl)phenylnonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-(trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyltetrafluoro-4- (trifluoromethyl)phenyl nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-2-pyridyl nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-3-pyridyl nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-4-pyridyl nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-2-benzonitrile nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-3-benzonitrile nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-4-benzonitrile pentafluorophenylpentafluorophenyl H pentafluorophenyl pentafluorophenyl CNpentafluorophenyl pentafluorophenyl F pentafluorophenylpentafluorophenyl Cl pentafluorophenyl pentafluorophenyl NO₂pentafluorophenyl pentafluorophenyl pentafluorophenyl pentafluorophenylpentafluorophenyl tetrafluoro-2- (trifluoromethyl)phenylpentafluorophenyl pentafluorophenyl tetrafluoro-3-(trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyltetrafluoro-4- (trifluoromethyl)phenyl pentafluorophenylpentafluorophenyl tetrafluoro-2-pyridyl pentafluorophenylpentafluorophenyl tetrafluoro-3-pyridyl pentafluorophenylpentafluorophenyl tetrafluoro-4-pyridyl pentafluorophenylpentafluorophenyl tetrafluoro-2-benzonitrile pentafluorophenylpentafluorophenyl tetrafluoro-3-benzonitrile pentafluorophenylpentafluorophenyl tetrafluoro-4-benzonitrile 4-pyrimidy 4-pyrimidy H4-pyrimidy 4-pyrimidy CN 4-pyrimidy 4-pyrimidy F 4-pyrimidy 4-pyrimidyCl 4-pyrimidy 4-pyrimidy NO₂ 4-pyrimidy 4-pyrimidy pentafluorophenyl4-pyrimidy 4-pyrimidy tetrafluoro-2- (trifluoromethyl)phenyl 4-pyrimidy4-pyrimidy tetrafluoro-3- (trifluoromethyl)phenyl 4-pyrimidy 4-pyrimidytetrafluoro-4- (trifluoromethyl)phenyl 4-pyrimidy 4-pyrimidytetrafluoro-2-pyridyl 4-pyrimidy 4-pyrimidy tetrafluoro-3-pyridyl4-pyrimidy 4-pyrimidy tetrafluoro-4-pyridyl 4-pyrimidy 4-pyrimidytetrafluoro-2-benzonitrile 4-pyrimidy 4-pyrimidytetrafluoro-3-benzonitrile 4-pyrimidy 4-pyrimidytetrafluoro-4-benzonitrile 2-pyrimidy 2-pyrimidy H 2-pyrimidy 2-pyrimidyCN 2-pyrimidy 2-pyrimidy F 2-pyrimidy 2-pyrimidy Cl 2-pyrimidy2-pyrimidy NO₂ 2-pyrimidy 2-pyrimidy pentafluorophenyl 2-pyrimidy2-pyrimidy tetrafluoro-2- (trifluoromethyl)phenyl 2-pyrimidy 2-pyrimidytetrafluoro-3- (trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyltetrafluoro-4- (trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyltetrafluoro-2-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-pyridyl2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl 2-pyrimidyl 2-pyrimidyltetrafluoro-2-benzonitrile 2-pyrimidyl 2-pyrimidyltetrafluoro-3-benzonitrile 2-pyrimidyl 2-pyrimidyltetrafluoro-4-benzonitrile 3,5- 3,5- H bis(trifluoromethyl)-bis(trifluoromethyl)- phenyl phenyl 3,5- trifluoromethyl Hbis(trifluoromethyl)- phenyl phenyl pentafluoroethyl H furan-2-yltrifluoromethyl H furan-2-yl pentafluoroethyl H 3,5- pentafluoroethyl Hbis(trifluoromethyl)- phenyl 3′,5′- pentafluoroethyl Hbis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 3′,5′- trifluoromethyl Hbis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 4-fluoro-3- pentafluoroethylH trifluoromethyl-phenyl 4-fluoro-3- 3,5- H trifluoromethyl-phenylbisftrifluoromethyl)- phenyl 3,4,5-trifluorophenyl 3,4,5-trifluorophenylH 3,4,5-trifluorophenyl pentafluoroethyl H 4- 4- H (trifluoromethyl)(trifluoromethyl) phenyl phenyl 4- pentafluoroethyl H (trifluoromethyl)phenyl 2,4,6- 2,4,6- H tris(trifluoromethyl) tris(trifluoromethyl)phenyl phenyl 2,4,6- Pentafluoroethyl H tris(trifluoromethyl) phenyl3,5- 3,5- CN bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl2,4,6- 2,4,6- CN tris(trifluoromethyl) tris(trifluoromethyl) phenylphenyl 3,5- pentafluoroethyl 3,5-bis(trifluoromethyl)-bis(trifluoromethyl)- phenyl phenyl 3,4- 3,4- H bis(trifluoromethyl)-bis(trifluoromethyl)- phenyl phenyl 3,4- trifluoromethyl Hbis(trifluoromethyl)- phenyl 3,4- pentafluoroethyl3,5-bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,4-pentafluoroethyl H bis(trifluoromethyl)- phenyl 3,4- 3,4- CNbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3-3,5- H (trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3-pentafluoroethyl H (trifluoromethyl)- phenyl 3,5- pentafluoroethyl CNbis(trifluoromethyl)- phenyl 4-cyano-2,6- 4-cyano-2,6- Hbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-2,6-pentafluoroethyl H bis(trifluoromethyl)- phenyl 2,4- 2,6- Hbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 2,4- 2,6- CNbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-(3′,5′-pentafluoroethyl H bis(trifluoromethyl) phenyl)-2,6-bis(trifluoromethyl)- phenyl phenyl phenyl CN 3,5- 3,5- CF₃bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,5-trifluoromethyl CF₃ bis(trifluoromethyl)- phenyl phenyl pentafluoroethylCF₃ 3,5- pentafluoroethyl CF₃ bis(trifluoromethyl)- phenyl3,4,5-trifluorophenyl 3,4,5-trifluorophenyl CF₃ 4- 4- CF₃(trifluoromethyl) (trifluoromethyl) phenyl phenyl phenyl phenyl CF₃


9. The electronic component according to claim 1, wherein the compoundsof formula (I.1) are selected from compounds of formula (I.a)

wherein R¹, R² and R³ are selected from R¹ R² R³ methyl methyl H methylmethyl CN methyl methyl F methyl methyl Cl methyl methyl NO₂ methylmethyl pentafluorophenyl methyl methyltetrafluoro-2-(trifluoromethyl)phenyl methyl methyltetrafluoro-3-(trifluoromethyl)phenyl methyl methyltetrafluoro-4-(trifluoromethyl)phenyl methyl methyltetrafluoro-2-pyridyl methyl methyl tetrafluoro-3-pyridyl methyl methyltetrafluoro-4-pyridyl methyl methyl tetrafluoro-2-benzonitrile methylmethyl tetrafluoro-3-benzonitrile methyl methyltetrafluoro-4-benzonitrile trifluoromethyl trifluoromethyl Htrifluoromethyl trifluoromethyl CN trifluoromethyl trifluoromethyl Ftrifluoromethyl trifluoromethyl Cl trifluoromethyl trifluoromethyl NO₂trifluoromethyl trifluoromethyl pentafluorophenyl trifluoromethyltrifluoromethyl tetrafluoro-2-(trifluoromethyl)phenyl trifluoromethyltrifluoromethyl tetrafluoro-3-(trifluoromethyl)phenyl trifluoromethyltrifluoromethyl tetrafluoro-4-(trifluoromethyl)phenyl trifluoromethyltrifluoromethyl tetrafluoro-2-pyridyl trifluoromethyl trifluoromethyltetrafluoro-3-pyridyl trifluoromethyl trifluoromethyltetrafluoro-4-pyridyl trifluoromethyl trifluoromethyltetrafluoro-2-benzonitrile trifluoromethyl trifluoromethyltetrafluoro-3-benzonitrile trifluoromethyl trifluoromethyltetrafluoro-4-benzonitrile pentafluoroethyl pentafluoroethyl Hpentafluoroethyl pentafluoroethyl CN pentafluoroethyl pentafluoroethyl Fpentafluoroethyl pentafluoroethyl Cl pentafluoroethyl pentafluoroethylNO₂ pentafluoroethyl pentafluoroethyl pentafluorophenyl pentafluoroethylpentafluoroethyl tetrafluoro-2-(trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-3-(trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-4-(trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-2-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-3-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-4-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-2-benzonitrile pentafluoroethyl pentafluoroethyltetrafluoro-3-benzonitrile pentafluoroethyl pentafluoroethyltetrafluoro-4-benzonitrile heptafluoro-n-propyl heptafluoro-n- H propylheptafluoro-n-propyl heptafluoro-n- CN propyl heptafluoro-n-propylheptafluoro-n- F propyl heptafluoro-n-propyl heptafluoro-n- Cl propylheptafluoro-n-propyl heptafluoro-n- NO₂ propyl heptafluoro-n-propylheptafluoro-n- pentafluorophenyl propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-2-(trifluoromethyl)phenyl propylheptafluoro-n-propyl heptafluoro-n-tetrafluoro-3-(trifluoromethyl)phenyl propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-4-(trifluoromethyl)phenyl propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-pyridyl propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-pyridyl propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-pyridyl propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-benzonitrile propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-benzonitrile propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-benzonitrile propylheptafluoro-isopropyl heptafluoro- H isopropyl heptafluoro-isopropylheptafluoro- CN isopropyl heptafluoro-isopropyl heptafluoro- F isopropylheptafluoro-isopropyl heptafluoro- Cl isopropyl heptafluoro-isopropylheptafluoro- NO₂ isopropyl heptafluor-iso-propyl heptafluoro-pentafluorophenyl isopropyl heptafluor-iso-propyl heptafluoro-tetrafluoro-2-(trifluoromethyl)phenyl isopropyl heptafluoro-isopropylheptafluoro- tetrafluoro-3-(trifluoromethyl)phenyl isopropylheptafluoro-isopropyl heptafluoro- tetrafluoro-4-(trifluoromethyl)phenylisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-pyridylisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-pyridylisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-pyridylisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-benzonitrileisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-benzonitrileisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-benzonitrileisopropyl tert-butyl tert-butyl H tert-butyl tert-butyl CN tert-butyltert-butyl F tert-butyl tert-butyl Cl tert-butyl tert-butyl NO₂tert-butyl tert-butyl pentafluorophenyl tert-butyl tert-butyltetrafluoro-2-(trifluoromethyl)phenyl tert-butyl tert-butyltetrafluoro-3-(trifluoromethyl)phenyl tert-butyl tert-butyltetrafluoro-4-(trifluoromethyl)phenyl tert-butyl tert-butyltetrafluoro-2-pyridyl tert-butyl tert-butyl tetrafluoro-3-pyridyltert-butyl tert-butyl tetrafluoro-4-pyridyl tert-butyl tert-butyltetrafluoro-2-benzonitrile tert-butyl tert-butyltetrafluoro-3-benzonitrile tert-butyl tert-butyltetrafluoro-4-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl Hnonafluoro-n-butyl nonafluoro-n-butyl CN nonafluoro-n-butylnonafluoro-n-butyl F nonafluoro-n-butyl nonafluoro-n-butyl Clnonafluoro-n-butyl nonafluoro-n-butyl NO₂ nonafluoro-n-butylnonafluoro-n-butyl pentafluorophenyl nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-2-(trifluoromethyl)phenylnonafluoro-n-butyl nonafluoro-n-butyltetrafluoro-3-(trifluoromethyl)phenyl nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-4-(trifluoromethyl)phenylnonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-pyridylnonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-pyridylnonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-pyridylnonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-benzonitrilenonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-benzonitrilenonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-benzonitrilepentafluorophenyl pentafluorophenyl H pentafluorophenylpentafluorophenyl CN pentafluorophenyl pentafluorophenyl Fpentafluorophenyl pentafluorophenyl Cl pentafluorophenylpentafluorophenyl NO₂ pentafluorophenyl pentafluorophenylpentafluorophenyl pentafluorophenyl pentafluorophenyltetrafluoro-2-(trifluoromethyl)phenyl pentafluorophenylpentafluorophenyl tetrafluoro-3-(trifluoromethyl)phenylpentafluorophenyl pentafluorophenyltetrafluoro-4-(trifluoromethyl)phenyl pentafluorophenylpentafluorophenyl tetrafluoro-2-pyridyl pentafluorophenylpentafluorophenyl tetrafluoro-3-pyridyl pentafluorophenylpentafluorophenyl tetrafluoro-4-pyridyl pentafluorophenylpentafluorophenyl tetrafluoro-2-benzonitrile pentafluorophenylpentafluorophenyl tetrafluoro-3-benzonitrile pentafluorophenylpentafluorophenyl tetrafluoro-4-benzonitrile 4-pyrimidyl 4-pyrimidyl H4-pyrimidyl 4-pyrimidyl CN 4-pyrimidyl 4-pyrimidyl F 4-pyrimidyl4-pyrimidyl Cl 4-pyrimidyl 4-pyrimidyl NO₂ 4-pyrimidyl 4-pyrimidylpentafluorophenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-2-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-3-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-4-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-2-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 4-pyrimidyl 4-pyrimidyltetrafluoro-2-benzonitrile 4-pyrimidyl 4-pyrimidyltetrafluoro-3-benzonitrile 4-pyrimidyl 4-pyrimidyltetrafluoro-4-benzonitrile 2-pyrimidyl 2-pyrimidyl H 2-pyrimidyl2-pyrimidyl CN 2-pyrimidyl 2-pyrimidyl F 2-pyrimidyl 2-pyrimidyl Cl2-pyrimidyl 2-pyrimidyl NO₂ 2-pyrimidyl 2-pyrimidyl pentafluorophenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-2-(trifluoromethyl)phenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-3-(trifluoromethyl)phenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-4-(trifluoromethyl)phenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-2-pyridyl 2-pyrimidyl 2-pyrimidyltetrafluoro-3-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl2-pyrimidyl 2-pyrimidyl tetrafluoro-2-benzonitrile 2-pyrimidyl2-pyrimidyl tetrafluoro-3-benzonitrile 2-pyrimidyl 2-pyrimidyltetrafluoro-4-benzonitrile 3,5- 3,5- H bis(trifluoromethyl)-bis(trifluoromethyl)- phenyl phenyl 3,5- trifluoromethyl Hbis(trifluoromethyl)- phenyl phenyl pentafluoroethyl H furan-2-yltrifluoromethyl H furan-2-yl pentafluoroethyl H 3,5- pentafluoroethyl Hbis(trifluoromethyl)- phenyl 3′,5′- pentafluoroethyl Hbis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 3′,5′- trifluoromethyl Hbis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 4-fluoro-3- pentafluoroethylH trifluoromethyl-phenyl 4-fluoro-3- 3,5- H trifluoromethyl-phenybis(trifluoromethyl)- phenyl 3,4,5-trifluorophenyl 3,4,5-trifluorophenylH 3,4,5-trifluorophenyl pentafluoroethyl H 4- 4- H(trifluoromethyl)phenyl (trifluoromethyl)phenyl 4- pentafluoroethyl H(trifluoromethyl)phenyl 2,4,6- 2,4,6- H tris(trifluoromethyl)phenyltris(trifluoromethyl)phenyl 2,4,6- Pentafluoroethyl Htris(trifluoromethyl)phenyl 3,5- 3,5- CN bis(trifluoromethyl)-bis(trifluoromethyl)- phenyl phenyl 2,4,6- 2,4,6- CNtris(trifluoromethyl)phenyl tris(trifluoromethyl)phenyl 3,5-pentafluoroethyl 3,5-bis(trifluoromethyl)-phenyl bis(trifluoromethyl)-phenyl 3,4- 3,4- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenylphenyl 3,4- trifluoromethyl H bis(trifluoromethyl)- phenyl 3,4-pentafluoroethyl 3,5-bis(trifluoromethyl)-phenyl bis(trifluoromethyl)-phenyl 3,4- pentafluoroethyl H bis(trifluoromethyl)- phenyl 3,4- 3,4- CNbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3-3,5- H (trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3-pentafluoroethyl H (trifluoromethyl)- phenyl 3,5- pentafluoroethyl CNbis(trifluoromethyl)- phenyl 4-cyano-2,6- 4-cyano-2,6- Hbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-2,6-pentafluoroethyl H bis(trifluoromethyl)- phenyl 2,4- 2,6- Hbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 2,4- 2,6- CNbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-(3′,5′-pentafluoroethyl H bis(trifluoro- methyl)phenyl)-2,6-bisftrifluoromethyl)- phenyl phenyl phenyl CN 3,5- 3,5- CF₃bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,5-trifluoromethyl CF₃ bis(trifluoromethyl)- phenyl phenyl pentafluoroethylCF₃ 3,5- pentafluoroethyl CF₃ bis(trifluoromethyl)- phenyl3,4,5-trifluorophenyl 3,4,5-trifluorophenyl CF₃ 4-4-(trifluoromethyl)phenyl CF₃ (trifluoromethyl)phenyl phenyl phenyl CF₃


10. The electronic component according to claim 1, wherein L₁, L₂, L₃and L₄ have the same meanings.
 11. The electronic component according toclaim 1 in form of an organic light-emitting diode, an organic solarcell, a photovoltaic cell, an organic diode or an organic transistor,preferably in form of a thin-film transistor, a Perovskite solar cell.12. The electronic component according to claim 1, having a layerstructure, which comprises 2, 3, 4, 5, 6, 7 or more layers.
 13. Theelectronic component according to claim 1, comprising an electrontransport layer, which comprises at least of the compound of formula(I.1).
 14. A doped semiconductor matrix material comprising at least oneelectron donor and at least one compound of the formula (I.1) or (I) asdefined in any one of claims 1 to 10, wherein the electron donor ispreferably selected from4,4′,4″-tris(N(2-naphthyl)-N-phenyl-amino)triphenylamine (2-TNATA),4,4′,4″-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine (m-MTDATA),N,N,N′,N′-tetrakis(4-methoxy-phenyl)benzidine (MeO-TPD),(2,2′,7,7′-tetrakis-(N,N-diphenylamino)-9,9′-spirobifluorene(spiro-TTB), N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-benzidine,N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)9,9-spiro-bifluorene,9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene,2,2′-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spiro-bifluorene,N,N′-((9H-fluoren-9,9-diyl)bis(4,1-phenylen))bis(N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4-amine)(BPAPF), N,N′-bis(phenanthren-9-yl)-N,N′-bis(phenyl)-benzidine,1,3,5-tris{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene,tri(terphenyl-4-yl)amine,N-(4-(6-((9,9-dimethyl-9H-fluoren-2-yl)(6-methoxy-[1,1′-biphenyl]-3-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)N-(6-methoxy-[1,1′-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine,N-([1,1′-biphenyl]-4-yl)-N-(4-(6-([1,1-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine,N,N-di([1,1-biphenyl]-4-yl)-3-(4-(di([1,1-biphenyl]-4-yl)amino)phenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine,N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine,N-(4-(6-(9,9′-spirobi[fluoren]-2-yl(9,9-dimethyl-9H-fluoren-2-Aamino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine,N-(4-(6-(dibenzo[b,d]furan-2-yl(9,9-dimethyl-9H-fluoren-2-Aamino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-2-amine,9-(4-(6-(9H-carbazol-9-yl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9H-carbazole,N-([1,1-biphenyl]-4-yl)-3-(4-([1,1-biphenyl]-4-yl(4-methoxyphenyl)amino)phenyl)-N-(4-methoxyphenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine,3-(4-(bis(6-methoxy-[1,1′-biphenyl]-3-yl)amino)phenyl)-N,N-bis(6-methoxy-[1,1-biphenyl]-3-yl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine,N1-([1,1-biphenyl]-4-yl)-N1-(4-(6-([1,1′-biphenyl]-4-yl(4-(diphenylamino)phenyl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N4,N4-diphenylbenzene-1,4-diamine,N,N-di([1,1-biphenyl]-4-yl)-4′-(6-(4-(di([1,1′-biphenyl]-4-yl)amino)phenyl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)-[1,1-biphenyl]-4-amine,N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine,N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine,N,N′-bis(9,9-dimethylfluoren-2-yl)-N,N′-diphenyl-benzidine (BF-DPB),N,N′-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1′-biphenyl]-4-yl)-[1,1-biphenyl]-4-amine)(BPAPF),N4,N4,N4′,N4′-tetrakis(9,9-dimethyl-9H-fluoren-2-yl)-[1,1-biphenyl]-4,4′-diamine(TDMFB),N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine,(2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluorene](spiro-MeO-TPD),a mixture ofN-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amineandN-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine,N-([1,1-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amineand mixtures thereof.
 15. A method for the production of organicsemiconductor, doping agent in organic semiconductor matrix materials,especially as p-dopant in hole transport layers, electron transportmaterial, charge injector in a charge injection layer, cathode materialin organic batteries, electrochromic material, wherein a compound (I.1)or mixtures thereof or of a compound (I) or mixtures thereof, as definedin any one of claims 1 to 10 is employed.
 16. A method for theproduction of organic conductor or as electrochromic material, whereinCe(III) complex anions obtained by reduction of a compound (I.1) or (I)as defined in any one of claims 1 to 10 or of charge transfer complexesof a compound (I.1) or (I) as defined in any one of claims 1 to 10 withelectron donors is employed.
 17. (canceled)
 18. A compound of thegeneral formula (I.1)Ce⁴⁺(L₁L₂L₃L₄)⁴⁻(I.1), and mixtures thereof, wherein L₁; L₂; L₃; and L₄are independently from each other a bidentate ligand having the generalformula (I.2)

wherein X and W independently from each other represent O or S; Yrepresents CR³⁻; R¹ represents A1

wherein where # denotes the bond to the remaining molecule of formula(I) and ligands of formula (I.2), R^(A), R^(B), R^(C), R^(D) and R^(E)are independently selected from hydrogen, CN, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl and phenyl, which is unsubstituted or substituted by 1,2 or 3 identical or different radicals selected from C₁-C₄-alkyl andC₁-C₄-haloalkyl; R² represents CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfanyl,C₁-C₆-haloalkylsulfanyl, NR^(4a)R^(4b); R³ represents hydrogen, CN,nitro and halogen; R^(4a)R^(4b) independently from each other representhydrogen, C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted orsubstituted by 1, 2, 3, 4 or 5 identical or different radicals R⁵⁻; R⁵represents CN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; or compounds offormula (I.a′)Ce⁴⁺[(R¹—C(O)═C(R³)—C(═O)—R²)(R^(1′)—C(—O)═C(R^(3′))—C(═O)—R^(2′))(R¹″—C(—O)═C(R³″)—C(═O)—R²″) (R^(1′)′-C(—O)═C(R^(3′)″—C(═O)—R^(2′)″)]⁴⁻(I.a′), wherein (R¹, R², R³), (R^(1′), R^(2′), R^(3′)), (R¹″, R²″, R³″)and (R^(1′)″, R^(2′)″, R^(3′)″) are each selected from the definitiongiven in one line of the following table R¹, R^(1′), R^(1″), R^(1′′′)R², R^(2′), R^(2″), R^(2′′′) R³, R^(3′), R^(3″), R^(3′′′) methyl methylCN methyl methyl F methyl methyl Cl methyl methyl NO₂ methyl methylpentafluorophenyl methyl methyl tetrafluoro-2- (trifluoromethyl)phenylmethyl methyl tetrafluoro-3- (trifluoromethyl)phenyl methyl methyltetrafluoro-4- (trifluoromethyl)phenyl methyl methyltetrafluoro-2-pyridyl methyl methyl tetrafluoro-3-pyridyl methyl methyltetrafluoro-4-pyridyl methyl methyl tetrafluoro-2-benzonitrile methylmethyl tetrafluoro-3-benzonitrile methyl methyltetrafluoro-4-benzonitrile trifluoromethyl trifluoromethyl CNtrifluoromethyl trifluoromethyl F trifluoromethyl trifluoromethyl Cltrifluoromethyl trifluoromethyl NO₂ trifluoromethyl trifluoromethylpentafluorophenyl trifluoromethyl trifluoromethyl tetrafluoro-2-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-3-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-4-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyltetrafluoro-2-pyridyl trifluoromethyl trifluoromethyltetrafluoro-3-pyridyl trifluoromethyl trifluoromethyltetrafluoro-4-pyridyl trifluoromethyl trifluoromethyltetrafluoro-2-benzonitrile trifluoromethyl trifluoromethyltetrafluoro-3-benzonitrile trifluoromethyl trifluoromethyltetrafluoro-4-benzonitrile pentafluoroethyl pentafluoroethyl Hpentafluoroethyl pentafluoroethyl CN pentafluoroethyl pentafluoroethyl Fpentafluoroethyl pentafluoroethyl Cl pentafluoroethyl pentafluoroethylNO₂ pentafluoroethyl pentafluoroethyl pentafluorophenyl pentafluoroethylpentafluoroethyl tetrafluoro-2- (trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-3- (trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-4- (trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-2-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-3-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-4-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-2-benzonitrile pentafluoroethyl pentafluoroethyltetrafluoro-3-benzonitrile pentafluoroethyl pentafluoroethyltetrafluoro-4-benzonitrile heptafluoro-n- heptafluoro-n- H propyl propylheptafluoro-n- heptafluoro-n- CN propyl propyl heptafluoro-n-heptafluoro-n- F propyl propyl heptafluoro-n- heptafluoro-n- Cl propylpropyl heptafluoro-n- heptafluoro-n- NO₂ propyl propyl heptafluoro-n-heptafluoro-n- pentafluorophenyl propyl propyl heptafluoro-n-heptafluoro-n- tetrafluoro-2- propyl propyl (trifluoromethyl)phenylheptafluoro-n- heptafluoro-n- tetrafluoro-3- propyl propyl(trifluoromethyl)phenyl heptafluoro-n- heptafluoro-n- tetrafluoro-4-propyl propyl (trifluoromethyl)phenyl heptafluoro-n- heptafluoro-n-tetrafluoro-2-pyridyl propyl propyl heptafluoro-n- heptafluoro-n-tetrafluoro-3-pyridyl propyl propyl heptafluoro-n- heptafluoro-n-tetrafluoro-4-pyridyl propyl propyl heptafluoro-n- heptafluoro-n-tetrafluoro-2-benzonitrile propyl propyl heptafluoro-n- heptafluoro-n-tetrafluoro-3-benzonitrile propyl propyl heptafluoro-n- heptafluoro-n-tetrafluoro-4-benzonitrile propyl propyl heptafluoro- heptafluoro- Hisopropyl isopropyl heptafluoro- heptafluoro- CN isopropyl isopropylheptafluoro- heptafluoro- F isopropyl isopropyl heptafluoro-heptafluoro- Cl isopropyl isopropyl heptafluoro- heptafluoro- NO₂isopropyl isopropyl heptafluor-iso- heptafluoro- pentafluorophenylpropyl isopropyl heptafluor-iso- heptafluoro- tetrafluoro-2- propylisopropyl (trifluoromethyl)phenyl heptafluoro- heptafluoro-tetrafluoro-3- isopropyl isopropyl (trifluoromethyl)phenyl heptafluoro-heptafluoro- tetrafluoro-4- isopropyl isopropyl (trifluoromethyl)phenylheptafluoro- heptafluoro- tetrafluoro-2-pyridyl isopropyl isopropylheptafluoro- heptafluoro- tetrafluoro-3-pyridyl isopropyl isopropylheptafluoro- heptafluoro- tetrafluoro-4-pyridyl isopropyl isopropylheptafluoro- heptafluoro- tetrafluoro-2-benzonitrile isopropyl isopropylheptafluoro- heptafluoro- tetrafluoro-3-benzonitrile isopropyl isopropylheptafluoro- heptafluoro- tetrafluoro-4-benzonitrile isopropyl isopropyltert-butyl tert-butyl CN tert-butyl tert-butyl F tert-butyl tert-butylCl tert-butyl tert-butyl NO₂ tert-butyl tert-butyl pentafluorophenyltert-butyl tert-butyl tetrafluoro-2- (trifluoromethyl)phenyl tert-butyltert-butyl tetrafluoro-3- (trifluoromethyl)phenyl tert-butyl tert-butyltetrafluoro-4- (trifluoromethyl)phenyl tert-butyl tert-butyltetrafluoro-2-pyridyl tert-butyl tert-butyl tetrafluoro-3-pyridyltert-butyl tert-butyl tetrafluoro-4-pyridyl tert-butyl tert-butyltetrafluoro-2-benzonitrile tert-butyl tert-butyltetrafluoro-3-benzonitrile tert-butyl tert-butyltetrafluoro-4-benzonitrile nonafluoro-n- nonafluoro-n- H butyl butylnonafluoro-n- nonafluoro-n- CN butyl butyl nonafluoro-n- nonafluoro-n- Fbutyl butyl nonafluoro-n- nonafluoro-n- Cl butyl butyl nonafluoro-n-nonafluoro-n- NO₂ butyl butyl nonafluoro-n- nonafluoro-n-pentafluorophenyl butyl butyl nonafluoro-n- nonafluoro-n- tetrafluoro-2-butyl butyl (trifluoromethyl)phenyl nonafluoro-n- nonafluoro-n-tetrafluoro-3- butyl butyl (trifluoromethyl)phenyl nonafluoro-n-nonafluoro-n- tetrafluoro-4- butyl butyl (trifluoromethyl)phenylnonafluoro-n- nonafluoro-n- tetrafluoro-2-pyridyl butyl butylnonafluoro-n- nonafluoro-n- tetrafluoro-3-pyridyl butyl butylnonafluoro-n- nonafluoro-n- tetrafluoro-4-pyridyl butyl butylnonafluoro-n- nonafluoro-n- tetrafluoro-2-benzonitrile butyl butylnonafluoro-n- nonafluoro-n- tetrafluoro-3-benzonitrile butyl butylnonafluoro-n- nonafluoro-n- tetrafluoro-4-benzonitrile butyl butylpentafluorophenyl pentafluorophenyl H pentafluorophenylpentafluorophenyl CN pentafluorophenyl pentafluorophenyl Fpentafluorophenyl pentafluorophenyl Cl pentafluorophenylpentafluorophenyl NO₂ pentafluorophenyl pentafluorophenylpentafluorophenyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-(trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyltetrafluoro-3- (trifluoromethyl)phenyl pentafluorophenylpentafluorophenyl tetrafluoro-4- (trifluoromethyl)phenylpentafluorophenyl pentafluorophenyl tetrafluoro-2-pyridylpentafluorophenyl pentafluorophenyl tetrafluoro-3-pyridylpentafluorophenyl pentafluorophenyl tetrafluoro-4-pyridylpentafluorophenyl pentafluorophenyl tetrafluoro-2-benzonitrilepentafluorophenyl pentafluorophenyl tetrafluoro-3-benzonitrilepentafluorophenyl pentafluorophenyl tetrafluoro-4-benzonitrile4-pyrimidyl 4-pyrimidyl H 4-pyrimidyl 4-pyrimidyl CN 4-pyrimidyl4-pyrimidyl F 4-pyrimidyl 4-pyrimidyl Cl 4-pyrimidyl 4-pyrimidyl NO₂4-pyrimidyl 4-pyrimidyl pentafluorophenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-2- (trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-3- (trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-4- (trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-2-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 4-pyrimidyl 4-pyrimidyltetrafluoro-2-benzonitrile 4-pyrimidyl 4-pyrimidyltetrafluoro-3-benzonitrile 4-pyrimidyl 4-pyrimidyltetrafluoro-4-benzonitrile 2-pyrimidyl 2-pyrimidyl H 2-pyrimidyl2-pyrimidyl CN 2-pyrimidyl 2-pyrimidyl F 2-pyrimidyl 2-pyrimidyl Cl2-pyrimidyl 2-pyrimidyl NO₂ 2-pyrimidyl 2-pyrimidyl pentafluorophenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-2- (trifluoromethyl)phenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-3- (trifluoromethyl)phenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-4- (trifluoromethyl)phenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-2-pyridyl 2-pyrimidyl 2-pyrimidyltetrafluoro-3-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl2-pyrimidyl 2-pyrimidyl tetrafluoro-2-benzonitrile 2-pyrimidyl2-pyrimidyl tetrafluoro-3-benzonitrile 2-pyrimidyl 2-pyrimidyltetrafluoro-4-benzonitrile 3,5- 3,5- H bis(trifluoro- bis(trifluoro-methyl)-phenyl methyl)-phenyl 3,5- trifluoromethyl H bis(trifluoro-methyl)-phenyl phenyl pentafluoroethyl H furan-2-yl pentafluoroethyl H3,5- pentafluoroethyl H bis(trifluoro- methyl)-phenyl 3′,5′-pentafluoroethyl H bis(trifluoro- methyl-[1,1′- biphenyl]-4-yl 3′,5′-trifluoromethyl H bis(trifluoro- methyl-[1,1′- biphenyl]-4-yl4-fluoro-3- pentafluoroethyl H trifluoromethyl- phenyl 4-fluoro-3- 3,5-H trifluoromethyl- bis(trifluoro- phenyl methyl)-phenyl 3,4,5- 3,4,5- Htrifluorophenyl trifluorophenyl 3,4,5- pentafluoroethyl Htrifluorophenyl 4- 4- H (trifluoro- (trifluoro- methyl)phenylmethyl)phenyl 4- pentafluoroethyl H (trifluoromethyl) phenyl 2,4,6-2,4,6- H tris(trifluoro- tris(trifluoro- methyl)phenyl methyl)phenyl2,4,6- Pentafluoroethyl H tris(trifluoro- methyl)phenyl 3,5- 3,5- CNbis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 2,4,6-2,4,6- CN tris(trifluoro- tris(trifluoro- methyl)phenyl methyl)phenyl3,5- pentafluoroethyl 3,5-bis(trifluoromethyl)- bis(trifluoro- phenylmethyl)-phenyl 3,4- 3,4- H bis(trifluoro- bis(trifluoro- methyl)-phenylmethyl)-phenyl 3,4- trifluoromethyl H bis(trifluoro- methyl)-phenyl 3,4-pentafluoroethyl 3,5-bis(trifluoromethyl)- bis(trifluoro- phenylmethyl)-phenyl 3,4- pentafluoroethyl H bis(trifluoro- methyl)-phenyl3,4- 3,4- CN bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl4-cyano-3- 3,5- H (trifluoro- bis(trifluoro methyl)-phenylmethyl)-phenyl 4-cyano-3- pentafluoroethyl H (trifluoro- methyl)-phenyl3,5- pentafluoroethyl CN bis(trifluoro- methyl)-phenyl 4-cyano-2,6-4-cyano-2,6- H bis(trifluoro- bis(trifluoro- methyl)-phenylmethyl)-phenyl 4-cyano-2,6- pentafluoroethyl H bis(trifluoro-methyl)-phenyl 2,4- 2,6- H bis(trifluoro- bis(trifluoro- methyl)-phenylmethyl)-phenyl 2,4- 2,6- CN bis(trifluoro- bis(trifluoro- methyl)-phenylmethyl)-phenyl 4-(3',5'- pentafluoroethyl H bis(trifluoro-methyl)phenyl)-2,6- bis(trifluoro- methyl)-phenyl phenyl phenyl CN 3,5-3,5- CF₃ bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl3,5- trifluoromethyl CF₃ bis(trifluoro- methyl)-phenyl phenylpentafluoroethyl CF₃ 3,5- pentafluoroethyl CF₃ bis(trifluoro-methyl)-phenyl 3,4,5- 3,4,5- CF₃ trifluorophenyl trifluorophenyl 4-4-(trifluoro- CF₃ (trifluoromethyl) methyl)phenyl phenyl phenyl phenylCF₃


19. (canceled)
 20. The compound according to claim 19 having the generalformula (I)

and their charge transfer complexes, their reduction products andmixtures thereof, wherein X and W independently from each otherrepresent O or S; Y represents CR³⁻; represents A1

wherein where # denotes the bond to the remaining molecule of formula(I), R^(A), R^(B), R^(C), R^(D) and R^(E) are independently selectedfrom hydrogen, CN, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and phenyl,which is unsubstituted or substituted by 1, 2 or 3 identical ordifferent radicals selected from C₁-C₄-alkyl and C₁-C₄-haloalkyl; R²represents CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfanyl, C₁-C₆-haloalkylsulfanyl,NR^(4a)R^(4b); R³ represents hydrogen, CN, nitro and halogen;R^(4a)R^(4b) independently from each other represent hydrogen,C₁-C₆-alkyl or C₆-C₁₄-aryl, wherein aryl is unsubstituted or substitutedby 1, 2, 3, 4 or 5 identical or different radicals R⁵⁻; R⁵ representsCN, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; or compounds of formula(I.a)

wherein the definition of R¹, R² and R³ listed in the following table:R¹ R² R³ methyl methyl CN methyl methyl F methyl methyl Cl methyl methylNO₂ methyl methyl pentafluorophenyl methyl methyltetrafluoro-2-(trifluoromethyl)phenyl methyl methyltetrafluoro-3-(trifluoromethyl)phenyl methyl methyltetrafluoro-4-(trifluoromethyl)phenyl methyl methyltetrafluoro-2-pyridyl methyl methyl tetrafluoro-3-pyridyl methyl methyltetrafluoro-4-pyridyl methyl methyl tetrafluoro-2-benzonitrile methylmethyl tetrafluoro-3-benzonitrile methyl methyltetrafluoro-4-benzonitrile trifluoromethyl trifluoromethyl CNtrifluoromethyl trifluoromethyl F trifluoromethyl trifluoromethyl Cltrifluoromethyl trifluoromethyl NO₂ trifluoromethyl trifluoromethylpentafluorophenyl trifluoromethyl trifluoromethyltetrafluoro-2-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyltetrafluoro-3-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyltetrafluoro-4-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyltetrafluoro-2-pyridyl trifluoromethyl trifluoromethyltetrafluoro-3-pyridyl trifluoromethyl trifluoromethyltetrafluoro-4-pyridyl trifluoromethyl trifluoromethyltetrafluoro-2-benzonitrile trifluoromethyl trifluoromethyltetrafluoro-3-benzonitrile trifluoromethyl trifluoromethyltetrafluoro-4-benzonitrile pentafluoroethyl pentafluoroethyl Hpentafluoroethyl pentafluoroethyl CN pentafluoroethyl pentafluoroethyl Fpentafluoroethyl pentafluoroethyl Cl pentafluoroethyl pentafluoroethylNO₂ pentafluoroethyl pentafluoroethyl pentafluorophenyl pentafluoroethylpentafluoroethyl tetrafluoro-2-(trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-3-(trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-4-(trifluoromethyl)phenyl pentafluoroethylpentafluoroethyl tetrafluoro-2-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-3-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-4-pyridyl pentafluoroethyl pentafluoroethyltetrafluoro-2-benzonitrile pentafluoroethyl pentafluoroethyltetrafluoro-3-benzonitrile pentafluoroethyl pentafluoroethyltetrafluoro-4-benzonitrile heptafluoro-n-propyl heptafluoro-n- H propylheptafluoro-n-propyl heptafluoro-n- CN propyl heptafluoro-n-propylheptafluoro-n- F propyl heptafluoro-n-propyl heptafluoro-n- Cl propylheptafluoro-n-propyl heptafluoro-n- NO₂ propyl heptafluoro-n-propylheptafluoro-n- pentafluorophenyl propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-2-(trifluoromethyl)phenyl propylheptafluoro-n-propyl heptafluoro-n-tetrafluoro-3-(trifluoromethyl)phenyl propyl heptafluoro-n-propylheptafluoro-n- tetrafluoro-4-(trifluoromethyl)phenyl propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-pyridyl propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-pyridyl propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-pyridyl propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-benzonitrile propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-benzonitrile propylheptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-benzonitrile propylheptafluoro-isopropyl heptafluoro- H isopropyl heptafluoro-isopropylheptafluoro- CN isopropyl heptafluoro-isopropyl heptafluoro- F isopropylheptafluoro-isopropyl heptafluoro- Cl isopropyl heptafluoro-isopropylheptafluoro- NO₂ isopropyl heptafluor-iso-propyl heptafluoro-pentafluorophenyl isopropyl heptafluor-iso-propyl heptafluoro-tetrafluoro-2-(trifluoromethyl)phenyl isopropyl heptafluoro-isopropylheptafluoro- tetrafluoro-3-(trifluoromethyl)phenyl isopropylheptafluoro-isopropyl heptafluoro- tetrafluoro-4-(trifluoromethyl)phenylisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-pyridylisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-pyridylisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-pyridylisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-benzonitrileisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-benzonitrileisopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-benzonitrileisopropyl tert-butyl tert-butyl CN tert-butyl tert-butyl F tert-butyltert-butyl Cl tert-butyl tert-butyl NO₂ tert-butyl tert-butylpentafluorophenyl tert-butyl tert-butyltetrafluoro-2-(trifluoromethyl)phenyl tert-butyl tert-butyltetrafluoro-3-(trifluoromethyl)phenyl tert-butyl tert-butyltetrafluoro-4-(trifluoromethyl)phenyl tert-butyl tert-butyltetrafluoro-2-pyridyl tert-butyl tert-butyl tetrafluoro-3-pyridyltert-butyl tert-butyl tetrafluoro-4-pyridyl tert-butyl tert-butyltetrafluoro-2-benzonitrile tert-butyl tert-butyltetrafluoro-3-benzonitrile tert-butyl tert-butyltetrafluoro-4-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl Hnonafluoro-n-butyl nonafluoro-n-butyl CN nonafluoro-n-butylnonafluoro-n-butyl F nonafluoro-n-butyl nonafluoro-n-butyl Clnonafluoro-n-butyl nonafluoro-n-butyl NO₂ nonafluoro-n-butylnonafluoro-n-butyl pentafluorophenyl nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-2-(trifluoromethyl)phenylnonafluoro-n-butyl nonafluoro-n-butyltetrafluoro-3-(trifluoromethyl)phenyl nonafluoro-n-butylnonafluoro-n-butyl tetrafluoro-4-(trifluoromethyl)phenylnonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-pyridylnonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-pyridylnonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-pyridylnonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-benzonitrilenonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-benzonitrilenonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-benzonitrilepentafluorophenyl pentafluorophenyl H pentafluorophenylpentafluorophenyl CN pentafluorophenyl pentafluorophenyl Fpentafluorophenyl pentafluorophenyl Cl pentafluorophenylpentafluorophenyl NO₂ pentafluorophenyl pentafluorophenylpentafluorophenyl pentafluorophenyl pentafluorophenyltetrafluoro-2-(trifluoromethyl)phenyl pentafluorophenylpentafluorophenyl tetrafluoro-3-(trifluoromethyl)phenylpentafluorophenyl pentafluorophenyltetrafluoro-4-(trifluoromethyl)phenyl pentafluorophenylpentafluorophenyl tetrafluoro-2-pyridyl pentafluorophenylpentafluorophenyl tetrafluoro-3-pyridyl pentafluorophenylpentafluorophenyl tetrafluoro-4-pyridyl pentafluorophenylpentafluorophenyl tetrafluoro-2-benzonitrile pentafluorophenylpentafluorophenyl tetrafluoro-3-benzonitrile pentafluorophenylpentafluorophenyl tetrafluoro-4-benzonitrile 4-pyrimidyl 4-pyrimidyl H4-pyrimidyl 4-pyrimidyl CN 4-pyrimidyl 4-pyrimidyl F 4-pyrimidyl4-pyrimidyl Cl 4-pyrimidyl 4-pyrimidyl NO₂ 4-pyrimidyl 4-pyrimidylpentafluorophenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-2-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-3-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-4-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyltetrafluoro-2-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 4-pyrimidyl 4-pyrimidyltetrafluoro-2-benzonitrile 4-pyrimidyl 4-pyrimidyltetrafluoro-3-benzonitrile 4-pyrimidyl 4-pyrimidyltetrafluoro-4-benzonitrile 2-pyrimidyl 2-pyrimidyl H 2-pyrimidyl2-pyrimidyl CN 2-pyrimidyl 2-pyrimidyl F 2-pyrimidyl 2-pyrimidyl Cl2-pyrimidyl 2-pyrimidyl NO₂ 2-pyrimidyl 2-pyrimidyl pentafluorophenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-2-(trifluoromethyl)phenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-3-(trifluoromethyl)phenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-4-(trifluoromethyl)phenyl2-pyrimidyl 2-pyrimidyl tetrafluoro-2-pyridyl 2-pyrimidyl 2-pyrimidyltetrafluoro-3-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl2-pyrimidyl 2-pyrimidyl tetrafluoro-2-benzonitrile 2-pyrimidyl2-pyrimidyl tetrafluoro-3-benzonitrile 2-pyrimidyl 2-pyrimidyltetrafluoro-4-benzonitrile 3,5- 3,5- H bis(trifluoromethyl)-bisftrifluoromethyl)- phenyl phenyl 3,5- trifluoromethyl Hbis(trifluoromethyl)- phenyl phenyl pentafluoroethyl H furan-2-ylpentafluoroethyl H 3,5- pentafluoroethyl H bis(trifluoromethyl)- phenyl3′,5′- pentafluoroethyl H bis(trifluoromethyl)- [1,1′-biphenyl]-4-yl3′,5′- trifluoromethyl H bis(trifluoromethyl)- [1,1′-biphenyl]-4-yl4-fluoro-3- pentafluoroethyl H trifluoromethyl-phenyl 4-fluoro-3- 3,5- Htrifluoromethyl-phenyl bisftrifluoromethyl)- phenyl3,4,5-trifluorophenyl 3,4,5-trifluorophenyl H 3,4,5-trifluorophenylpentafluoroethyl H 4- 4- H (trifluoromethyl)phenyl(trifluoromethyl)phenyl 4- pentafluoroethyl H (trifluoromethyl)phenyl2,4,6- 2,4,6- H tris(trifluoromethyl)phenyl tris(trifluoromethyl)phenyl2,4,6- Pentafluoroethyl H tris(trifluoromethyl)phenyl 3,5- 3,5- CNbis(trifluoromethyl)- bisftrifluoromethyl)- phenyl phenyl 2,4,6- 2,4,6-CN tris(trifluoromethyl)phenyl tris(trifluoromethyl)phenyl 3,5-pentafluoroethyl 3,5-bis(trifluoromethyl)-phenyl bis(trifluoromethyl)-phenyl 3,4- 3,4- H bis(trifluoromethyl)- bisftrifluoromethyl)- phenylphenyl 3,4- trifluoromethyl H bis(trifluoromethyl)- phenyl 3,4-pentafluoroethyl 3,5-bis(trifluoromethyl)-phenyl bis(trifluoromethyl)-phenyl 3,4- pentafluoroethyl H bis(trifluoromethyl)- phenyl 3,4- 3,4- CNbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3-3,5- H (trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3-pentafluoroethyl H (trifluoromethyl)- phenyl 3,5- pentafluoroethyl CNbis(trifluoromethyl)- phenyl 4-cyano-2,6- 4-cyano-2,6- Hbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-2,6-pentafluoroethyl H bis(trifluoromethyl)- phenyl 2,4- 2,6- Hbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 2,4- 2,6- CNbis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-(3′,5′-pentafluoroethyl H bis(trifluoro- methyl)phenyl)-2,6-bis(trifluoromethyl)- phenyl phenyl phenyl CN 3,5- 3,5- CF₃bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,5-trifluoromethyl CF₃ bis(trifluoromethyl)- phenyl phenyl pentafluoroethylCF₃ 3,5- pentafluoroethyl CF₃ bis(trifluoromethyl)- phenyl3,4,5-trifluorophenyl 3,4,5-trifluorophenyl CF₃ 4- 4-(trifluoro- CF₃(trifluoromethyl)phenyl methyl)phenyl phenyl phenyl CF₃